One-pot synthesis of multi-substituted conjugated dienones by trapping allene carbocations with active ylides

Dan Ni; Longlong Song; Yun Zhao; Shunying Liu

doi:10.1039/d1cc06405c

One-pot synthesis of multi-substituted conjugated dienones by trapping allene carbocations with active ylides

Chem Commun (Camb). 2022 Feb 22;58(16):2698-2701. doi: 10.1039/d1cc06405c.

Authors

Dan Ni¹, Longlong Song¹, Yun Zhao¹, Shunying Liu¹

Affiliation

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China. syliu@sist.ecnu.edu.cn.

PMID: 35108717
DOI: 10.1039/d1cc06405c

Abstract

A Rh(II)/boron reagent co-catalyzed unprecedent transformation was established for the rapid construction of multi-substituted conjugated dienones under mild conditions by trapping allene carbocations with oxonium ylides from simple starting points in yields up to 85%. Two CC double bonds, one C-C and one C-O single bond were built in this one-pot reaction. The diversity-oriented strategy was also established to synthesize alkyne ether and dihydrofuran derivatives by a substrate-depended fashion.