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

Versatile and mild: The first general method for the title transformation has been developed (see scheme; 2‐F‐Py=2‐fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the reduction. This method should find application...

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Published inAngewandte Chemie International Edition Vol. 51; no. 33; pp. 8314 - 8317
Main Authors Xiao, Kai-Jiong, Wang, Ai-E, Huang, Pei-Qiang
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 13.08.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Activated
Alkylation
amide activation
Amides
Amides - chemistry
Amines
Amines - chemical synthesis
Amines - chemistry
Anhydrides
Biocompatibility
cerium
Chemistry
Chemistry, Multidisciplinary
CC bond formation
Molecular Structure
Physical Sciences
Reduction
Reductive alkylation
Science & Technology
Synthesis
synthetic methods
Transformations
PYRIDINE-DERIVATIVES
cerium
amines
TERTIARY AMIDES
SEQUENTIAL ADDITION-REACTIONS
NUCLEOPHILIC CYCLIZATIONS
C?C bond formation
amide activation
MAGNESIUM REAGENTS
ARYL AMIDES
VILSMEIER-HAACK
synthetic methods
GRIGNARD-REAGENTS
ORGANOLITHIUM
ALKALOIDS
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Summary:Versatile and mild: The first general method for the title transformation has been developed (see scheme; 2‐F‐Py=2‐fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the reduction. This method should find applications in the synthesis of nitrogen‐containing bioactive molecules and medicinal agents.
Bibliography:NSF - No. 21072160; No. 20832005
ark:/67375/WNG-72Q5N2RB-S
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.
Fundamental Research Funds - No. 201112G001
istex:B3A8B235012624317632531E46EECDECCAF0E532
National Basic Research Program - No. 2010CB833200
ArticleID:ANIE201204098
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.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201204098