A Traceless Directing Group for CH Borylation
2013; Wiley; Volume: 52; Issue: 49 Linguagem: Inglês
10.1002/anie.201306511
ISSN1521-3773
AutoresSean Preshlock, Donald L. Plattner, Peter E. Maligres, Shane W. Krska, Robert E. Maleczka, Milton R. Smith,
Tópico(s)Catalytic Cross-Coupling Reactions
ResumoAngewandte Chemie International EditionVolume 52, Issue 49 p. 12915-12919 Communication A Traceless Directing Group for CH Borylation† Sean M. Preshlock, Sean M. Preshlock Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)Search for more papers by this authorDonald L. Plattner, Donald L. Plattner Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)Search for more papers by this authorDr. Peter E. Maligres, Dr. Peter E. Maligres Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)Search for more papers by this authorDr. Shane W. Krska, Corresponding Author Dr. Shane W. Krska [email protected] Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA) Shane W. Krska, Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)=== Robert E. Maleczka, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)=== Milton R. Smith, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)===Search for more papers by this authorProf. Dr. Robert E. Maleczka Jr., Corresponding Author Prof. Dr. Robert E. Maleczka Jr. [email protected] Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA) Shane W. Krska, Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)=== Robert E. Maleczka, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)=== Milton R. Smith, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)===Search for more papers by this authorProf. Dr. Milton R. Smith III, Corresponding Author Prof. Dr. Milton R. Smith III [email protected] Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA) Shane W. Krska, Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)=== Robert E. Maleczka, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)=== Milton R. Smith, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)===Search for more papers by this author Sean M. Preshlock, Sean M. Preshlock Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)Search for more papers by this authorDonald L. Plattner, Donald L. Plattner Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)Search for more papers by this authorDr. Peter E. Maligres, Dr. Peter E. Maligres Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)Search for more papers by this authorDr. Shane W. Krska, Corresponding Author Dr. Shane W. Krska [email protected] Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA) Shane W. Krska, Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)=== Robert E. Maleczka, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)=== Milton R. Smith, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)===Search for more papers by this authorProf. Dr. Robert E. Maleczka Jr., Corresponding Author Prof. Dr. Robert E. Maleczka Jr. [email protected] Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA) Shane W. Krska, Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)=== Robert E. Maleczka, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)=== Milton R. Smith, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)===Search for more papers by this authorProf. Dr. Milton R. Smith III, Corresponding Author Prof. Dr. Milton R. Smith III [email protected] Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA) Shane W. Krska, Department of Process Chemistry, Merck Research Laboratories, Rahway, NJ 07065 (USA)=== Robert E. Maleczka, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)=== Milton R. Smith, Department of Chemistry, Michigan State University, 578 S Shaw Lane, East Lansing, MI 48824-1322 (USA)===Search for more papers by this author First published: 12 November 2013 https://doi.org/10.1002/anie.201306511Citations: 153 † We thank the NSF (GOALI-1012883), the NIH (GM63188), and the ACS Green Chemistry Institute Pharmaceutical Roundtable for generous financial support. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation 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 Graphical Abstract Not a trace: Borylation of the nitrogen in nitrogen heterocycles or anilines provides a traceless directing group for subsequent catalytic CH borylation. Selectivities that previously required Boc protection can be achieved; furthermore, the NBpin directing group can be installed and removed in situ, and product yields are substantially higher. Boc=tert-butoxycarbonyl, pin=pinacolato. References 1S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529– 531. 2 2aD. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624– 655; 2bT. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147– 1169. 3I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890– 931. 4 4aT. Ishiyama, H. Isou, T. Kikuchi, N. Miyaura, Chem. Commun. 2009, 159– 161; 4bS. Kawamorita, H. Ohmiya, K. Hara, A. Fukuoka, M. Sawamura, J. Am. Chem. Soc. 2009, 131, 5058– 5059; 4cS. 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