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

• Published in: Angewandte Chemie International Edition Vol. 51; no. 33; pp. 8314 - 8317
• Main Authors: Xiao, Kai-Jiong, Wang, Ai-E, Huang, Pei-Qiang
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 13.08.2012; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International 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

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...