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Transition‐Metal‐Free α Csp 3 −H Cyanation of Sulfonamides
Author(s) -
Zhou Liejin,
Wei Siqi,
Lei Ziran,
Zhu Gangguo,
Zhang Zuxiao
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100902
Subject(s) - imine , chemistry , strecker amino acid synthesis , combinatorial chemistry , cyanation , surface modification , selectivity , transition metal , organic chemistry , catalysis , enantioselective synthesis
This report describes the site‐selective α‐functionalization of sulfonylamide derivatives through the in‐situ generation of imine intermediates. The N−F sulfonylamides, which could facilitate the elimination to generate imines, are coupled with TBACN to efficiently and mildly afford α‐amino cyanides. Comparing with Strecker reaction, this transformation offers a complementary strategy to efficiently construct α‐amino cyanides from direct α C−H functionalization of sulfonylamindes. The reaction is also characterized by broad substrate scope and flash chromatography column free workup. More importantly, the new two‐electron pathway to generate imines through manipulation of the leaving group allows us to achieve excellent α site‐selectivity.