Cross-Coupling between Difluorocarbene and Carbene-Derived Intermediates Generated from Diazocompounds for the Synthesis of gem-Difluoroolefins

• DOI: 10.1021/acs.orglett.5b03159
• Publication Date: 2015-12-04T17:05:18Z
• Authors: Jian Zheng; Jin-Hong Lin; Liu-Ying Yu; Yun Wei; Xing Zheng; Ji-Chang Xiao
• Keywords: 01 natural sciences; 0104 chemical sciences

Cross-coupling between difluorocarbene and carbene-derived intermediates generated from diazocompounds was developed to give gem-difluoroolefins, which constitutes a fast practical pathway to achieve hindered gem-difluoroolefins. The cross-coupling between difluorocarbene and aryl diazoacetates proceeded smoothly in the presence of a copper source, whereas its coupling with diaryl diazomethanes occurred well under metal-free conditions. A mechanism involving a copper-difluorocarbene complex was proposed.