Phosphine-catalysed intermolecular cyclopropanation reaction between benzyl bromides and activated alkenes. (10th August 2022)

• Record Type: Journal Article
• Authors: Zhang, Jie; Song, Xue; Chen, Zhi-Chao; Du, Wei; Chen, Ying-Chun
• Is Part Of: New journal of chemistry. Volume 46:Number 34(2022)
• Page Start: 16382
• Page End: 16386
• Publication Date: 2022-08-10
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj03417d
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : An intermolecular cyclopropanation reaction between benzyl bromides and activated alkenes was reported catalysed by a bifunctional phosphine. Abstract : While phosphine-mediated reactions have been extensively explored over the past few decades, the catalytic cyclopropanation reaction via a phosphonium ylide pathway has been significantly underdeveloped, and an intermolecular version still remains to be disclosed. Presented herein is a catalytic cyclopropanation reaction between readily available benzyl bromides and activated alkenes, such as α-cyano chalcones, through in situ formation of phosphonium ylide intermediates. A spectrum of densely functionalized cyclopropane derivatives is efficiently constructed with excellent diastereoselectivity, which can be further converted to five-membered heterocycles after simple transformations. Moreover, moderate enantioselectivity can be obtained by using a commercially available DuPhos catalyst.