CF2Br2 as a Source for Difluoroolefination of 1,3-Enynes via N-Heterocyclic Carbene Catalysis

Lei Chen; Jingyi Wang; Chen Lin; Yiwei Zhu; Ding Du

doi:10.1021/acs.orglett.2c03007

CF₂Br₂ as a Source for Difluoroolefination of 1,3-Enynes via N-Heterocyclic Carbene Catalysis

Org Lett. 2022 Sep 30;24(38):7047-7051. doi: 10.1021/acs.orglett.2c03007. Epub 2022 Sep 19.

Authors

Lei Chen¹, Jingyi Wang¹, Chen Lin¹, Yiwei Zhu², Ding Du¹

Affiliations

¹ State Key Laboratory of Natural Medicines, School of Science, China Pharmaceutical University, Nanjing, 210009, P.R. China.
² School of Chemistry and Environmental Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000, P.R. China.

PMID: 36121666
DOI: 10.1021/acs.orglett.2c03007

Abstract

Commercially available CF₂Br₂ has been used as a convenient source for the rapid and reliable incorporation of the gem-difluorovinyl motif into an allene framework via an N-heterocyclic carbene catalyzed difluoroolefination of 1,3-enynes. The reaction proceeds through a cascade three-component radical relay/elimination process. This protocol is distinguished by its mild conditions, readily accessible starting materials, wide substrate scope, and ease of late-stage functionalization, thus unlocking an untraditional strategy to construct a new class of functionalized gem-difluorovinyl allenes.