Soft propargylic deprotonation: Designed ligand enables au-catalyzed isomerization of alkynes to 1,3-Dienes

Zhixun Wang, Yanzhao Wang, Liming Zhang

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3′ position, the derived gold(I) complex possesses orthogonally positioned "push" and "pull" forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of >26 pKa units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions.

Original languageEnglish (US)
Pages (from-to)8887-8890
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number25
DOIs
StatePublished - Jun 25 2014

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