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Synthesis of Vinyl‐ and Aryl–Acyl Sulfonimidamides Through Pd‐Catalyzed Carbonylation Using Mo(CO) 6 as ex situ CO Source
Author(s) -
Wakchaure Prasad B.,
Borhade Sanjay R.,
Sandström Anja,
Arvidsson Per I.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403148
Subject(s) - carbonylation , chemistry , electrophile , aryl , nucleophile , catalysis , reagent , halide , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl , carbon monoxide
We report the synthesis of N ‐(α,β‐unsaturated acyl)‐substituted sulfonimidamides through a Pd‐catalyzed carbonylation protocol, employing sulfonimidamides as nucleophiles using CO gas released ex situ, and vinyl/aryl halides and triflates as reagents. The reaction is general and offers a unique class of products in moderate to good yields for a wide range of substrates and electrophiles; for example, aliphatic, aromatic (electron‐donating and ‐withdrawing groups), heteroaryl, vinyl halides, and triflates. We also expand our initial report on N ‐aryl–acyl‐substituted sulfonimidamide synthesis by employing aryltriflates as electrophiles. Furthermore, we report a surprisingly facile thermolytic Boc deprotection of N ‐(α,β‐unsaturated acyl) sulfonimidamides.