z-logo
Premium
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom