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  • One pot iridium-catalyzed asymmetrical double allylations of sodium sulfide: a fast and economic way to construct chiral C2-symmetric bis(1-substituted-allyl)sulfane.

One pot iridium-catalyzed asymmetrical double allylations of sodium sulfide: a fast and economic way to construct chiral C2-symmetric bis(1-substituted-allyl)sulfane.

Chemical communications (Cambridge, England) (2011-05-20)
Shengcai Zheng, Weiqing Huang, Ning Gao, Ruimin Cui, Min Zhang, Xiaoming Zhao
ABSTRACT

One pot asymmetrical double allylations of sodium sulfide catalyzed by an iridium complex along with a combination of caesium fluoride and water in dichloromethane have been realized and the double allylation products with two C-S bond chiral centers were obtained in 67-99% yields with b/l 81/19-99/1, dr 85/15-99/1, and 96-99% ee.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cesium fluoride, BioUltra, ≥99.0% (F)
Sigma-Aldrich
Cesium fluoride, purum p.a., ≥98.0%
Sigma-Aldrich
Cesium fluoride, 99.9% trace metals basis
Sigma-Aldrich
Cesium fluoride, 99%
Sigma-Aldrich
Cesium fluoride, 99.99% trace metals basis
Sigma-Aldrich
Cesium Fluoride ChemBeads, NSC 84270