Premium
Cross‐Coupling of Grignard Reagents with Sulfonyl‐Activated sp 3 Carbon‐Nitrogen Bonds
Author(s) -
Li ManBo,
Tang XiangLing,
Tian ShiKai
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100285
Subject(s) - chemistry , sulfonyl , reagent , allylic rearrangement , stereoselectivity , amine gas treating , iodide , coupling reaction , medicinal chemistry , alkyne , organic chemistry , combinatorial chemistry , catalysis , alkyl
Sulfonyl‐activated sp 3 carbon‐nitrogen bonds have been found to be cleaved by Grignard reagents in the presence of 5 mol% of copper(I) iodide (CuI). Significantly, a broad range of sulfonyl‐activated benzylic, allylic, and propargylic amines smoothly undergo the cross‐coupling reaction with Grignard reagents to afford structurally diverse coupling products in good to excellent yields and with high chemo‐, regio‐, and stereoselectivity. Moreover, an S N 2 mechanism has been demonstrated to be involved in the cross‐coupling reaction that allows the asymmetric synthesis of chiral hydrocarbons from optically active α‐branched amine derivatives.