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Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation

2012; Wiley; Volume: 124; Issue: 33 Linguagem: Inglês

10.1002/ange.201204098

1521-3757

Kai‐Jiong Xiao, Ai‐E Wang, Pei‐Qiang Huang,

Asymmetric Hydrogenation and Catalysis

Angewandte ChemieVolume 124, Issue 33 p. 8439-8442 Zuschrift Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation† Kai-Jiong Xiao, Kai-Jiong Xiao Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Search for more papers by this authorDr. Ai-E Wang, Dr. Ai-E Wang Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Search for more papers by this authorProf. Dr. Pei-Qiang Huang, Corresponding Author Prof. Dr. Pei-Qiang Huang pqhuang@xmu.edu.cn Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Search for more papers by this author Kai-Jiong Xiao, Kai-Jiong Xiao Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Search for more papers by this authorDr. Ai-E Wang, Dr. Ai-E Wang Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Search for more papers by this authorProf. Dr. Pei-Qiang Huang, Corresponding Author Prof. Dr. Pei-Qiang Huang pqhuang@xmu.edu.cn Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (P.R. China)Search for more papers by this author First published: 13 July 2012 https://doi.org/10.1002/ange.201204098Citations: 59 † The authors are grateful to the National Basic Research Program (973 Program) of China (Grant No. 2010CB833200), the NSF of China (21072160; 20832005), and the Fundamental Research Funds for the Central Universities of China (Grant No. 201112G001)for financial support, and for a Scholarship Award for Excellent Doctoral Student granted by Ministry of Education of China (2010). We are grateful to Prof. Dr. G. M. Blackburn for valuable discussions and to Y.-H. for the preparation of some starting materials. Read the full textAboutPDF 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 onFacebookTwitterLinkedInRedditWechat Graphical Abstract Vielseitig und mild: Die erste allgemeine Methode für die Titelreaktion (siehe Schema; 2-F-Py=2-Fluorpyridin; Tf=Trifluorsulfonyl) liefert die Amine in guten Ausbeuten, wobei die Ketimin-Zwischenstufen vor der Reduktion isoliert werden können. Die Methode sollte in der Synthese von stickstoffhaltigen biologisch aktiven Molekülen und medizinischen Wirkstoffen Verwendung finden. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description ange_201204098_sm_miscellaneous_information.pdf939.8 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume124, Issue33August 13, 2012Pages 8439-8442 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. RelatedInformation