| Literature DB >> 24328754 |
Dinesh Nath1, Melanie C Skilbeck, Iain Coldham, Fraser F Fleming.
Abstract
The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to α-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.Entities:
Year: 2013 PMID： 24328754 DOI： 10.1021/ol403020s
Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005