Übergangsmetall-katalysierte Synthese von Arylaminen und Arylethern aus Arylhalogeniden und -triflaten: Anwendungen und Reaktionsmechanismus
1998; Wiley; Volume: 110; Issue: 15 Linguagem: Alemão
10.1002/(sici)1521-3757(19980803)110
ISSN1521-3757
Autores Tópico(s)Chemical Synthesis and Reactions
ResumoAngewandte ChemieVolume 110, Issue 15 p. 2154-2177 Aufsatz Übergangsmetall-katalysierte Synthese von Arylaminen und Arylethern aus Arylhalogeniden und -triflaten: Anwendungen und Reaktionsmechanismus John F. Hartwig, John F. Hartwig [email protected] Department of Chemistry, Yale University, P.O. Box 208107, New Haven, CT 06520-8107, USA, Fax: (+1) 203-432-6144Search for more papers by this author John F. Hartwig, John F. Hartwig [email protected] Department of Chemistry, Yale University, P.O. Box 208107, New Haven, CT 06520-8107, USA, Fax: (+1) 203-432-6144Search for more papers by this author First published: August 3, 1998 https://doi.org/10.1002/(SICI)1521-3757(19980803)110:15 3.0.CO;2-CCitations: 331AboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Oxidative Addition und reduktive Eliminierung sind die zentralen Schritte bei neuen Pd-katalysierten Reaktionen zur Bildung von C-N- und C-O-Bindungen von Arylaminen bzw. -ethern. Im nebenstehenden Mechanismusvorschlag wird ein Amin durch reduktive Eliminierung aus einem vierfach koordinierten 16-Elektronen-Amidoarylkomplex gebildet. Die Verwendung eines chelatisierenden Liganden wie 1,1′-Bis(diphenylphosphanyl)ferrocen (dppf) verringert dabei das Ausmaß der konkurrierenden β-Wasserstoffeliminierung. X=Br, I; R, R′=Alkyl, Aryl. References 1 R. A. Glennon, J. Med. Chem. 1987, 30, 1–12. 10.1021/jm00384a001 CASPubMedWeb of Science®Google Scholar 2 H. Hugel, D. J. Kennaway, Org, Prep. Priced. Int. 1995, 27, CASGoogle Scholar 3 D. H. R. Barton, D. M. X. Donnelly, J. Finet, P. J. Guiry, J. M. Kielty, Tetrahedron Lett. 1990, 46, 6637–6640. 10.1016/S0040-4039(00)97134-X Web of Science®Google Scholar 4 G. J. S. Doad, J. A. Barltrop, C. M. Petty, T. C. Owen, Tetrahedron Lett. 1989, 30, 1597–1598. 10.1016/S0040-4039(00)99529-7 CASWeb of Science®Google Scholar 5 K. Hiroya, K. Hashimura, K. Ogasawara, Heterocycles 1994, 38, 2463–2472. 10.3987/COM-94-6874 CASWeb of Science®Google Scholar 6 J. Setsune, T. Ueda, K. Shikata, K. Matsukawa, T. Iida, T. Kitao, Tetrahedron Lett. 1986, 42, 2647–2656. 10.1016/S0040-4020(01)90550-2 CASWeb of Science®Google Scholar 7 D. L. Boger, D. Yohannes, Tetrahedron Lett. 1989, 30, 2053–2056. 10.1016/S0040-4039(01)93709-8 CASWeb of Science®Google Scholar 8 D. L. Boger, D. Yohannes, J. Org. Chem. 1990, 55, 6000–6011. 10.1021/jo00311a019 CASWeb of Science®Google Scholar 9 D. L. Boger, D. Yohannes, J. Am. Chem. Soc. 1991, 113, 1427–1429. 10.1021/ja00004a062 CASWeb of Science®Google Scholar 10 D. L. Boger, D. Yohannes, J. Zhou, M. A. Patane, J. Am. Chem. Soc. 1993, 115, 3420–3430. 10.1021/ja00062a004 CASWeb of Science®Google Scholar 11 D. L. Boger, J. Zhou, J. Am. Chem. Soc. 1993, 115, 11426–11433. 10.1021/ja00077a047 CASWeb of Science®Google Scholar 12 D. A. Evans, J. A. Ellman, J. Am. Chem. Soc. 1989, 111, 1063–1072. 10.1021/ja00185a042 CASWeb of Science®Google Scholar 13 H. Itokawa, K. Takeya, Heterocycles 1993, 35, 1467–1501. 10.3987/REV-92-SR(T)7 CASWeb of Science®Google Scholar 14 A. J. Pearson, J. G. Park, J. Org. Chem. 1992, 57, 1744–1752. 10.1021/jo00032a028 CASWeb of Science®Google Scholar 15 S. Nishiyama, K. Nakamura, Y. Susuki, S. Yamamura, Tetrahedron Lett. 1986, 27, 4481–4484. 10.1016/S0040-4039(00)84984-9 CASWeb of Science®Google Scholar 16 T. Kato, Y. Suzumura, S. Takamoto. K. Ota, Anticancer Res. 1987, 7, 329–334. CASPubMedWeb of Science®Google Scholar 17 K. Matsuzaki, H. Ikeda, T. Ogino, A. Matsumoto, H. B. Woodruff, H. Tanaka, S. Omura, J. Antibiotics 1994, 47, 1173–1174. 10.7164/antibiotics.47.1173 CASPubMedWeb of Science®Google Scholar 18 M. Nagai, M. Kubo, M. Fujita, T. Oki, J. Antibiotics 1993, 46, 1812–1817. 10.7164/antibiotics.46.520 Google Scholar 19 N. Naruse, M. Oka, M. Konishi, T. Oki, J. Antibiotics 1993, 46, 1812–1817. 10.7164/antibiotics.46.1812 CASPubMedWeb of Science®Google Scholar 20 A. J. Pearson, K. S. Lee, J. Org. Chem. 1994, 59, 2304–2313. 10.1021/jo00088a009 CASWeb of Science®Google Scholar 21 A. Kitani, M. Kaya, J. Yano, K. Yoshikawa, K. Sasaki, Synth. Met. 1987, 18, 341. 10.1016/0379-6779(87)90902-7 CASWeb of Science®Google Scholar 22 F.-L. Lu, F. Wudl, M. Nowak, A. J. Heeger, J. Am. Chem. Soc. 1986, 108, 8311. 10.1021/ja00286a057 CASWeb of Science®Google Scholar 23 A. G. MacDiarmid, J. C. Chiang, A. F. Richter, A. J. Epstein, Synth. Met. 1987, 18, 285–290. 10.1016/0379-6779(87)90893-9 CASWeb of Science®Google Scholar 24 A. G. MacDiarmid, A. J. Epstein, Faraday Discuss. Chem. Soc. 1989, 88, 317–332. 10.1039/dc9898800317 CASWeb of Science®Google Scholar 25 A. G. MacDiarmid, A. J. Epstein in Science and Applications of Conducting Polymers (Hrsg.: W. R. Salaneck, D. T. Clark, E. J. Samuslsen), Hilger, New York, 1991, S. 117. Web of Science®Google Scholar 26 A. Ray, A. F. Richter, D. L. Kershner, A. J. Epstein, Synth. Met. 1989, 29, E141–E150. 10.1016/0379-6779(89)90289-0 CASWeb of Science®Google Scholar 27 D. Vachon, R. O. Angus, F. L. Lu, M. Nowak, Z. X. Liu, H. Schaffer, F. Woudl, A. J. Heeger, Synth. Met. 1987, 18, 297. 10.1016/0379-6779(87)90895-2 CASWeb of Science®Google Scholar 28 M. Stolka, J. F. Yanus, D. M. Pai, J. Phys. Chem. 1984, 88, 4707. 10.1021/j150664a053 CASWeb of Science®Google Scholar 29 E. Ueta, H. Nakano, Y. Shirota, Chem Lett. 1994, 2397–2400. Google Scholar 30 Y. Kuwabara, H. Ogawa, H. Inada, N. Noma, Y. Shirota, Adv. Mater. 1994, 6, 677. 10.1002/adma.19940060913 CASWeb of Science®Google Scholar 31 M. Strukelj, R. H. Jordan, A. Dodabalapur, J. Am. Chem. Soc. 1996, 118, 1213–1214. 10.1021/ja953302n CASWeb of Science®Google Scholar 32 P. E. Cassidy, Thermally Stable Polymers: Synthesis and Properties, Marcel Dekker, New York, 1980. Google Scholar 33 T. M. Miller, T. X. Neenan, E. W. Kwock, S. M. Stein, J. Am. Chem. Soc. 1993, 115, 356–357. 10.1021/ja00054a057 CASWeb of Science®Google Scholar 34 A. P. Melissaris, M. H. Litt, Macromolecules 1994, 27, 888–892. 10.1021/ma00082a002 CASWeb of Science®Google Scholar 35 J. A. Irvin, C. J. Neef, K. M. Kane, P. E. Cassidy, G. Tullos, A. K.St. Clair, J. Polym. Sci. Part A: Polym. Chem. 1992, 30, 1675–1679. 10.1002/pola.1992.080300820 CASWeb of Science®Google Scholar 36 J. March, Advanced Organic Chemistry, 3. Aufl., Wiley, New York, 1985. Google Scholar 37 G. W. Gribble, P. D. Lord, J. Skotnicki, S. E. Dietz, J. T. Eaton, J. L. Johnson, J. Am. Chem. Soc. 1974, 96, 7812–7814. 10.1021/ja00832a035 CASWeb of Science®Google Scholar 38 P. Marchini, G. Liso, A. Reho, J. Org. Chem. 1975, 40, 3453–3456. 10.1021/jo00911a038 CASWeb of Science®Google Scholar 39 C. F. Lane, Synthesis 1975 135–146. Google Scholar 40 J. Lindley, Tetrahedron 1984, 40, 1456. 10.1016/S0040-4020(01)91791-0 Web of Science®Google Scholar 41 H. L. Aalten, G. van Koten, D. M. Grove, Tetrahedron 1989, 45, 5565–5578. 10.1016/S0040-4020(01)89502-8 CASWeb of Science®Google Scholar 42 A. J. Paine, J. Am. Chem. 1987, 109, 1496–1502. 10.1021/ja00239a032 CASWeb of Science®Google Scholar 43 H. Weingarten, J. Org. Chem. 1964, 29, 977–978. 10.1021/jo01027a529 CASWeb of Science®Google Scholar 44 H. Heaney, Chem. Rev. 1962, 62, 81–97. 10.1021/cr60216a001 CASWeb of Science®Google Scholar 45 R. Rossi, R. H. de Rossi, Aromatic Substitution by the Srn1 Mechanism, Vol. 178, American Chemical Society, Washington, DC, 1983. Google Scholar 46 J. E. Shaw, D. C. Kunerth, S. B. Swanson, J. Org. Chem. 1976, 41, 732–733. 10.1021/jo00866a043 CASWeb of Science®Google Scholar 47 A. J. Pearson, J. G. Park, S. H. Yang, Y.-H. Chuang, J. Chem. Soc. Chem. Commun. 1989 1363–1364. Google Scholar 48 J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987. Google Scholar 49 J. K. Stille, Angew. Chem. 1986, 98, 504–519; 10.1002/ange.19860980605 CASGoogle Scholar Angew. Chem. Int. Ed. Engl. 1986, 25, 508–524. 10.1002/anie.198605081 Web of Science®Google Scholar 50 J. K. Stille, Pure Appl. Chem. 1985, 57, 1771–1780. 10.1351/pac198557121771 CASWeb of Science®Google Scholar 51 A. Suzuki, Pure Appl. Chem. 1994, 66, 213. 10.1351/pac199466020213 CASWeb of Science®Google Scholar 52 A. Suzuki, Pure Appl. Chem 1985, 57, 1749. 10.1351/pac198557121749 CASWeb of Science®Google Scholar 53 N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457–2483. 10.1021/cr00039a007 CASWeb of Science®Google Scholar 54 E. Negishi, Acc. Chem. Res. 1982, 15, 340–348. 10.1021/ar00083a001 CASWeb of Science®Google Scholar 55 T. Hayashi, Y. Hagihara, Y. Katsuro, M. Kumada, Bull. Chem. Soc. Jpn. 1983, 56, 363–364. 10.1246/bcsj.56.363 CASWeb of Science®Google Scholar 56 T. N. Nitchell, Synthesis 1992 803–815. Google Scholar 57 D. Barañano, G. Mann, J. F. Hartwig, Curr. Org. Chem. 1997, 1, 287–305. 10.1016/S1367-5931(97)80063-4 CASWeb of Science®Google Scholar 58 D. Cai, J. F. Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 7180–7181. 10.1021/jo00102a059 CASWeb of Science®Google Scholar 59 D. Baranano, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 2937–2938. 10.1021/ja00115a033 CASWeb of Science®Google Scholar 60 K. Takagi, Chem. Lett. 1987, 2221–2224. Google Scholar 61 M. Kosugi, T. Ogata, M. Terad, H. Sano, T. Migita, Bull. Chem. Soc. Jpn. 1985, 58, 3657–3658. 10.1246/bcsj.58.3657 CASWeb of Science®Google Scholar 62 H. J. Cristau, B. Chabaud, A. Chéne, H. Christol, Synthesis 1981, 892–894. Google Scholar 63 J. P. Collman. L. S. Hegedus, J. R. Norton, R. G. Finke in Principles and Applications of Organotransition Metal Chemistry, 2. Aufl., University Science Books, Mill Valley, CA, 1987, S. 279–354. Google Scholar 64 R. H. Crabtree, Chem. Rev. 1995, 95, 987–1007. 10.1021/cr00036a005 CASWeb of Science®Google Scholar 65 S.-Y. Liou, M. Gozin, D. Milstein, J. Am. Chem. Soc. 1995, 117, 9774–9775, zit. Lit. 10.1021/ja00143a028 CASWeb of Science®Google Scholar 66 S. Y. Liou, M. Gozin, D. Milstein, J. Chem. Soc. Chem. Commun. 1995, 1965–1966. Google Scholar 67 M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 4708–4709. 10.1021/ja00121a030 CASWeb of Science®Google Scholar 68 M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1996, 118, 7217–7218. 10.1021/ja960937t CASWeb of Science®Google Scholar 69 G. Mann, J. Hartwig, J. Am. Chem. Soc. 1996, 118, 13109–13110. 10.1021/ja963273w CASWeb of Science®Google Scholar 70 L. A. Villanueva, K. A. Abboud, J. M. Boncella, Organometallics 1994, 13, 3921–2931. 10.1021/om00022a031 CASWeb of Science®Google Scholar 71 K. Koo, G. L. Hillhouse, Organometallics 1995, 14, 4421–4423. 10.1021/om00009a054 CASWeb of Science®Google Scholar 72 P. T. Matsunaga, J. C. Mavropoulos, G. L. Hillhouse, Polyhedron 1995, 14, 175–185. 10.1016/0277-5387(94)00330-H CASWeb of Science®Google Scholar 73 E. G. Bryan, B. F. G. Johnson, J. Lewis, J. Chem. Soc. Dalton Trans. 1977, 1328–1330. Google Scholar 74 M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1996, 108, 4206–4207. 10.1021/ja954129y Web of Science®Google Scholar 75 M. D. Fryzuk, C. D. Montgomery, Coord. Chem. Rev. 1989, 95, 1–40. 10.1016/0010-8545(89)80001-3 CASWeb of Science®Google Scholar 76 H. Bryndza, W. Tam, Chem. Rev. 1988, 88, 1163–1188. 10.1021/cr00089a009 CASWeb of Science®Google Scholar 77 P. M. Henry, Palladium Catalyzed Oxidation of Hydrocarbons, Vol. 2 Reidel, Boston, 1980. Google Scholar 78 Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes (Hrsg.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996. 10.1002/9783527619351 Google Scholar 79 R. A. Sheldon, J. K. Kochi, Metal Catalyzed Oxidations of Organic Compounds: Mechanistic Principles and Synthetic Methodology Including Biochemical Processes, Acadmic Press, New York, 1981. Google Scholar 80 G. Cainelli, Chromium Oxidations in Organic Chemistry, Springer, New York, 1984. 10.1007/978-3-642-69362-5 Google Scholar 81 M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108–4109. 10.1021/ja00193a056 CASWeb of Science®Google Scholar 82 M. R. Gagné, S. P. Nolan, T. J. Marks, Organometallics 1990, 9, 1716–1718. 10.1021/om00156a005 CASWeb of Science®Google Scholar 83 A. L. Casalnuovo, J. C. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738–6744, zit. Lit. 10.1021/ja00228a022 CASWeb of Science®Google Scholar 84übersichtsartikel: B. R. James, Chem. Ind. 1995, 62, 167–180. CASWeb of Science®Google Scholar 85 M. D. Fryzuk, M. Kameyama, T. Migita, Chem. Lett. 1983, 9 986–98. Google Scholar 86 M. Kosugi, M. Kameyama, T. Migita, Chem. Lett. 1983, 927–928. Google Scholar 87 M. Kosugi, M. Kameyama, H. Sano, T. Migita, Nippon Kagaku Kaishi 1985, 3, 547–551. 10.1246/nikkashi.1985.547 Google Scholar 88 D. L. Boger, J. S. Panek, Tetrahedron Lett. 1984, 25, 3175–3178. 10.1016/S0040-4039(01)91001-9 CASWeb of Science®Google Scholar 89 D. L. Boger, S. R. Duff, J. S. Panek, M. Yasuda, J. Am. Chem. Soc. 1985, 50, 5790–5795. CASWeb of Science®Google Scholar 90 D. L. Boger, S. R. Duff, J. S. Panek, M. Yasuda, J. Org. Chem. 1985, 50, 5782–5789. 10.1021/jo00350a069 CASWeb of Science®Google Scholar 91 F. Paul, J. Patt, J. F. Hartwig, J. Am. Chem. Soc. 1994, 116, 5969–5970. 10.1021/ja00092a058 CASWeb of Science®Google Scholar 92 A. S. Guram, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 7901–7902. 10.1021/ja00096a059 CASWeb of Science®Google Scholar 93 J. Louie, J. F. Hartwig, Tetrahedron Lett. 1995, 36, 3609–3612. 10.1016/0040-4039(95)00605-C CASWeb of Science®Google Scholar 94 A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. 1995, 107, 1456–1459; 10.1002/ange.19951071216 Google Scholar Angew. Chem. Int. Ed. Engl. 1995, 34, 1343–1350. 10.1002/anie.199513431 CASWeb of Science®Google Scholar 95 S. Zhao, A. K. Miller, J. Berger, L. A. Flippin, Tetrahedron Lett. 1996, 37, 4463–4466. 10.1016/0040-4039(96)00877-5 CASWeb of Science®Google Scholar 96 J. P. Wolfe, S. L. Buchwald, J. Org. Chem. 1996, 61, 1133–1135. 10.1021/jo951844h CASWeb of Science®Google Scholar 97 J. P. Wolfe, R. A. Rennels, S. L. Buchwald, Tetrahedron 1996, 52, 7525–7546. 10.1016/0040-4020(96)00266-9 CASWeb of Science®Google Scholar 98 M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 8232–8245. 10.1021/ja971057x CASWeb of Science®Google Scholar 99 J. F. Hartwig, J. Am. Chem. Soc. 1996, 118, 7010–7011. 10.1021/ja961439n CASWeb of Science®Google Scholar 100 T. Hayashi, M. Konoshi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 1984, 106, 158–163. 10.1021/ja00313a032 CASWeb of Science®Google Scholar 101 J. P. Wolfe, S. Wagaw, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 7215–7216. 10.1021/ja9608306 CASWeb of Science®Google Scholar 102 J. F. Marcoux, R. Widenhoefer, A. Zhong, S. L. Buchwald, vorgetragen auf dem 213th American Chemical Society National Meeting, San Francisco, CA, 1997. Google Scholar 103 B. C. Bamann, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 12382–12383. 10.1021/ja9727880 Web of Science®Google Scholar 104 J.-F. Marcoux, S. Wagaw, S. L. Buchwald, J. Org. Chem. 1997, 62, 1562–1569. 10.1021/jo9622946 Web of Science®Google Scholar 105 J. C. Jeffrey, T. B. Rauchfuss, Inorg. Chem. 1979, 18, 2658–2666. 10.1021/ic50200a004 CASWeb of Science®Google Scholar 106 K. Takagi, Y. Sakakibara, Chem. Lett. 1989, 1957–1958. Google Scholar 107 S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1986, 27, 3931–3934. 10.1016/S0040-4039(00)83920-9 CASWeb of Science®Google Scholar 108 J. Louie, M. S. Driver, B. C. Hamann, J. F. Hartwig, J. Org. Chem. 1997, 62, 1268–1273. 10.1021/jo961930x CASWeb of Science®Google Scholar 109 J. P. Wolfe, S. L. Buchwald, J. Org. Chem. 1997, 62, 1264–1267. 10.1021/jo961915s CASWeb of Science®Google Scholar 110 V. Farina, B. Krishnan, D. R. Marshall, G. P. Roth, J. Org. Chem. 1993, 58, 5434–5444, zit. Lit. 10.1021/jo00072a028 CASWeb of Science®Google Scholar 111 V. Snieckus, Chem. Rev. 1990, 90, 879–933. 10.1021/cr00104a001 CASWeb of Science®Google Scholar 112 J. Louie, J. F. Hartwig, unveröffentlichte Ergebnisse. Google Scholar 113 F. Paul, J. Patt, J. F. Hartwig, Organometallics 1995, 14, 3030–3039. 10.1021/om00006a053 CASGoogle Scholar 114 S. Wagaw, S. L. Buchwald, J. Org. Chem. 1996, 61, 7240–7241. 10.1021/jo9612739 CASPubMedWeb of Science®Google Scholar 115 C. A. Willoughby, K. T. Chapman, Tetrahedron Lett. 1996, 37, 7181–7184. 10.1016/0040-4039(96)01633-4 CASWeb of Science®Google Scholar 116 Y. D. Ward, V. Farina, Tetrahedron Lett. 1996, 67, 6993–6996. 10.1016/0040-4039(96)01566-3 Google Scholar 117 P. H. H. Hermkens, H. C. J. Ottenheijm, D. Rees, Tetrahedron 1997, 52, 4527–4554. 10.1016/0040-4020(96)00216-5 Web of Science®Google Scholar 118 A. J. Peat, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 1028–1030. 10.1021/ja953080t CASWeb of Science®Google Scholar 119 T. Kanbara, A. Honma, K. Hasegawa, Chem. Lett. 1996, 1135–1136. Google Scholar 120 J. Louie, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 11695–11696. 10.1021/ja972806d CASWeb of Science®Google Scholar 121 M. Palucki, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 10333–10334. 10.1021/ja962408v CASWeb of Science®Google Scholar 122 G. Mann, J. F. Hartwig, J. Org. Chem. 1997, 62, 5413–5418. 10.1021/jo970453v CASWeb of Science®Google Scholar 123 M. Palucki, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 3395–3396. 10.1021/ja9640152 CASWeb of Science®Google Scholar 124 Die Herstellung lieferte nur Gemische aus L2Pd und L2PdC12 in geringen Ausbeuten (einziges Zitat in den Chemical Abstracts hierzu): S. Enomoto, H. Wada, S. Nishida, Y. Mukaida, M. Yanaka, H. Takita, Jpn. Kokai Tokkyo Koho, 1978, Google Scholar 7pp (JP-A 53144552, Google Scholar [ Chem. Abstr. 1979, 90, p2055124y ]). Google Scholar 125 S. Otsuka, T. Yoshida, M. Matsumoto, K. Nakatsu, J. Am. Chem. Soc. 1976, 98, 5850–5858. 10.1021/ja00435a017 CASWeb of Science®Google Scholar 126 T. Yoshida, S. Otsuka, J. Am. Chem. Soc. 1977, 99, 2134–2140. 10.1021/ja00449a019 CASWeb of Science®Google Scholar 127 T. Yoshida, S. Otsuka, Inorg. Synth. 1990, 28, 113–119. 10.1002/9780470132593.ch30 CASWeb of Science®Google Scholar 128 A. Davis, J. F. Hartwig, unveröffentlichte Ergebnisse. Google Scholar 129 M. Saunders, L. Telkowski, M. R. Kates, J. Am. Chem. Soc. 1977, 99, 8070–8071. 10.1021/ja00466a060 CASWeb of Science®Google Scholar 130 R. B. Calvert, J. R. Shapley, J. Am. Chem. Soc. 1978, 100, 7726–7727. 10.1021/ja00492a047 CASWeb of Science®Google Scholar 131 M. Brookhart, M. L. H. Green, L.-L. Wong, Prog. Inorg. Chem. 1988, 36, 1–124. 10.1002/9780470166376.ch1 CASWeb of Science®Google Scholar 132 M. Brookhart, M. L. H. Green, Organomet. Chem. 1983, 250, 295–408. 10.1016/0022-328X(83)85065-7 Web of Science®Google Scholar 133 J. F. Hartwig, F. Paul, J. Am. Chem. Soc. 1995, 117, 5373–5374. 10.1021/ja00124a026 CASWeb of Science®Google Scholar 134 E. Negishi, T. Takahashi, K. Akiyoshi, J. Chem. Soc. Chem. Commun. 1986, 1338. Google Scholar 135 Für eine Zusammenfassung dieser Mechanismen und der zugehörigen Daten siehe: C. Amatore, F. Pfluger, Organometallics 1990, 9, 2276–2282. 10.1021/om00158a026 CASWeb of Science®Google Scholar 136 C. Amatore, A. Jutand, A. Suarez, J. Am. Chem. Soc. 1993, 115, 9531–9541. 10.1021/ja00074a018 CASWeb of Science®Google Scholar 137 J. K. Stille, K. S. Y. Lau, Acc. Chem. Res. 1977, 10, 434–442. 10.1021/ar50120a002 CASWeb of Science®Google Scholar 138 A. Gillie, J. K. Stille, J. Am. Chem. Soc. 1980, 102, 4933–4941. 10.1021/ja00535a018 CASWeb of Science®Google Scholar 139 A. Moraviskiy, J. K. Stille, J. Am. Chem. Soc. 1981, 103, 4182–4186. 10.1021/ja00404a034 Web of Science®Google Scholar 140 C. Mateo, D. J. Cárdenas, C. Fernádez-Rivas, A. M. Echavarren, Chem. Eur. J. 1996, 2, 1596–1606. 10.1002/chem.19960021219 CASWeb of Science®Google Scholar 141 V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585–9595. 10.1021/ja00025a025 CASWeb of Science®Google Scholar 142 J. Louie, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 11598–11599. 10.1021/ja00151a033 CASWeb of Science®Google Scholar 143 R. A. Widenhoefer, S. L. Buchwald, Organometallics 1996, 15, 3534–3642. 10.1021/om9603169 CASWeb of Science®Google Scholar 144 R. A. Widenhoefer, S. L. Buchwald, Organometallics 1996, 15, 2755–2763. 10.1021/om9509608 CASWeb of Science®Google Scholar 145 R. A. Widenhorfer, H. A. Zhong, S. L. Buchwald, Organometallics 1996, 15, 2745–2754. 10.1021/om9509599 Web of Science®Google Scholar 146 J. Louie, F. Paul, J. F. Hartwig, Organometallics 1996, 15, 2794–3005. 10.1021/om960188o CASWeb of Science®Google Scholar 147 A. Streitweiser, Jr., Persönliche Mitteilung, 1997. Google Scholar 148 M. S. Driver, J. F. Hartwig, Organometallics 1997, 16, 5706–5715. 10.1021/om970856l CASWeb of Science®Google Scholar 149 J. F. Hartwig, G. Mann, unveröffentlichte Ergebnisse. Google Scholar 150 Die Verwendung von binap in der Arbeitsgruppe von Buchwald wurd durch Untersuchungen zur kinetischen Racematspaltung chiraler Amine ausgelöst. Google Scholar 151 P. T. Matsunaga, C. R. Hess, G. L. Hillhouse, J. Am. Chem. Soc. 1993, 115, 2075–2077. 10.1021/ja00058a085 CASWeb of Science®Google Scholar 152 K. Koo, G. L. Hillhouse, Organometallics 1996, 15, 2669–2671. 10.1021/om960286+ CASWeb of Science®Google Scholar 153 P. T. Matsunaga, G. L. Hillhouse, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 2075–2077. 10.1021/ja00058a085 CASWeb of Science®Google Scholar 154 H. E. Bryndza, L. K. Kong, R. A. Paciello, W. Tam, J. E. Bercaw, J. Am. Chem. Soc. 1987, 109, 1444–1456. 10.1021/ja00239a026 CASWeb of Science®Google Scholar 155 J. B. Cannon, J. Schwartz, J. Am. Chem. Soc. 1974, 96, 2276–2278. 10.1021/ja00814a062 Web of Science®Google Scholar 156 J. Evans, J. Schwartz. P. W. Urquhart, J. Organomer. Chem. 1985, S. 559. Google Scholar 157 R. J. Cross in The Chemistry of the Metal-Carbon Bond, Vol. 2 (Hrsg.: F. R. Hartley, S. Patai), Wiley, New York, 1985, S. 559. 10.1002/9780470771747.ch8 Google Scholar 158 G. M. Whitesides, J. F. Gaasch, E. R. Stedronsky, J. Am. Chem. Soc. 1972, 94, 5258–5270. 10.1021/ja00770a021 CASWeb of Science®Google Scholar 159 H. S. Hesslink, J. F. Hartwig, unveröffentlichte Ergebnisse. Google Scholar 160 J. F. Hartwig, S. Richards, D. Barañano, F. Paul, J. Am. Chem. Soc. 1996, 118, 3626–3633. 10.1021/ja954121o CASWeb of Science®Google Scholar 161 W. D. Jones, V. L. Kuykendall, Inorg. Chem 1991, 30, 2615–2622. 10.1021/ic00012a010 CASWeb of Science®Google Scholar 162 J. M. Brown, P. J. Guiry, Inorg. Chim. Acta 1994, 220, 249–259. 10.1016/0020-1693(94)03876-7 CASWeb of Science®Google Scholar 163 Wir haben kürzlich sowohl mit dppf als auch mit binap Spaltungen des Ligandengerüsts beobachtet. L. Alcazar-Roman, J. F. Hartwig, unveröffentlichte Ergebnisse. Google Scholar 164 M. Nishiyama, T. Yamamoto, Y. Koie, Tetrohedron Lett. 1998, 39, 617–620. 10.1016/S0040-4039(97)10659-1 CASWeb of Science®Google Scholar 165 K. Rossen, P. J. Pye, A. Maliakal, R. P. Volante, J. Org. Chem. 1997, 62, 6462–6463. 10.1021/jo971300a CASWeb of Science®Google Scholar 166 J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 6054–6058. 10.1021/ja964391m CASWeb of Science®Google Scholar 167 N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807–4810. 10.1016/S0040-4039(97)01038-1 CASWeb of Science®Google Scholar 168 M. Beller, T. H. Reirmeier, C. Reisinger, W. A. Herrmann, Tetrahedron Lett. 1997, 38, 2073–2074. 10.1016/S0040-4039(97)00289-X CASWeb of Science®Google Scholar 169 Y. P. Hong, G. J. Tanoury, H. S. Wilkinson, R. P. Bakale, S. A. Wald, C. H. Senanayake, Tetrahedron Lett. 1997, 38, 5663–5666. 10.1016/S0040-4039(97)01233-1 Web of Science®Google Scholar 170 J. P. Wolfe, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6359–6362. 10.1016/S0040-4039(97)01463-9 CASWeb of Science®Google Scholar 171 J. Åhman, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6363–6366. 10.1016/S0040-4039(97)01464-0 CASWeb of Science®Google Scholar 172 J. P. Wolfe, J. Åhman, J. P. Sadighi, R. A. Singer, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6367–6370. 10.1016/S0040-4039(97)01465-2 CASWeb of Science®Google Scholar 173 S. Darses, J.-P. Genêoct, J.-L. Brayer, J.-P. Demoute, Tetrahedron Lett. 1997, 38, 4393–4396. 10.1016/S0040-4039(97)00939-8 CASWeb of Science®Google Scholar 174 J. P. Wolfe, S. L. Buchwald, J. Org. Chem. 1997, 62, 6066–6068. 10.1021/jo970876x CASWeb of Science®Google Scholar 175 D. Ma, J. Yao, Tetrahedron: Asymmetry 1996, 7, 3075–3078. 10.1016/0957-4166(96)00401-6 CASWeb of Science®Google Scholar 176 S. Wagaw, R. A. Rennels, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 8451–8458. 10.1021/ja971583o CASWeb of Science®Google Scholar 177 I. P. Beletskaya, A. G. Bessermertnykh, R. Guilard, Tetrahedron Lett. 1997, 38, 2287–2290. 10.1016/S0040-4039(97)00363-8 CASWeb of Science®Google Scholar 178 R. A. Singer, J. P. Sadighi, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 213–214. 10.1021/ja973407l CASWeb of Science®Google Scholar 179 R. A. Widenhoefer, H. A. Zhong, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 6787–6795. 10.1021/ja963324p CASWeb of Science®Google Scholar 180 R. Han, G. L. Hillhouse, J. Am. Chem. Soc. 1997, 119, 8135–8136. 10.1021/ja9714999 CASWeb of Science®Google Scholar 181 F. E. Goodson, J. F. Hartwig, Macromolecules 1998, 31, 1700–1703. 10.1021/ma980027r CASWeb of Science®Google Scholar 182 G. Mann, J. F. Hartwig, Tetrahedron Lett. 1997, 38, 8005–8008. 10.1016/S0040-4039(97)10175-7 CASWeb of Science®Google Scholar 183 G. Mann, M. S. Driver, C. Fernández-Rivas, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 827–828. 10.1021/ja973524g CASWeb of Science®Google Scholar 184 J. F. Hartwig, Angew. Chem. 1998, 110, 2249–2252; 10.1002/(SICI)1521-3757(19980803)110:15 3.0.CO;2-F Google Scholar Angew. Chem. Int. Ed. 1998, 37, 2090–2093. 10.1002/(SICI)1521-3773(19980817)37:15 3.0.CO;2-A CASWeb of Science®Google Scholar Citing Literature Volume110, Issue15August 3, 1998Pages 2154-2177 This is the German version of Angewandte Chemie. 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