We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Palladium/Copper-Catalyzed Oxidative Arylation of Terminal Alkenes with Aroyl Hydrazides.
- Authors
Zhang, Yong‐Gang; Liu, Xiang‐Lei; He, Zeng‐Yang; Li, Xi‐Ming; Kang, Hong‐Jian; Tian, Shi‐Kai
- Abstract
An unprecedented oxidative arylation reaction of terminal alkenes with simple aroyl hydrazides has been developed under aerobic conditions for the stereoselective synthesis of 1,2-disubstituted alkenes. A range of aroyl hydrazides underwent palladium/copper-catalyzed oxidative Mizoroki-Heck reaction with terminal alkenes open to air in a 1:1 mixture of dimethyl sulfoxide and acetonitrile to give structurally diverse 1,2-disubstituted alkenes in moderate to excellent yields with excellent regio- and E-selectivity. The reaction tolerated a wide variety of functional groups, such as alkoxy, hydroxy, amino, fluoro, chloro, bromo, cyano, nitro, ester, amide, imide, phosphine oxide, and sulfone groups, and, moreover, molecular oxygen and dimethyl sulfoxide were demonstrated to serve as terminal oxidants. This study provides a useful method for the stereoselective synthesis of 1,2-disubstituted alkenes through direct transformation of the vinylic CH bonds in terminal alkenes.
- Subjects
PALLADIUM catalysts; COPPER catalysts; ARYLATION; ALKENE synthesis; HYDRAZIDES
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 10, p2765
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201304696