(Z)-Selective Synthesis of Bromofluoroalkenes via the TMSCF2Br-Mediated Tandem Reaction with para-Quinone Methides

Jie Zhu; Menghua Xu; Baihui Gong; Aijun Lin; Shang Gao

doi:10.1021/acs.orglett.3c01007

(Z)-Selective Synthesis of Bromofluoroalkenes via the TMSCF₂Br-Mediated Tandem Reaction with para-Quinone Methides

Org Lett. 2023 May 12;25(18):3271-3275. doi: 10.1021/acs.orglett.3c01007. Epub 2023 Apr 27.

Authors

Jie Zhu¹, Menghua Xu¹, Baihui Gong¹, Aijun Lin¹, Shang Gao¹

Affiliation

¹ State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 210009, P. R. China.

PMID: 37104568
DOI: 10.1021/acs.orglett.3c01007

Abstract

We report herein a tandem reaction of para-quinone methides with TMSCF₂Br to construct bromofluoroalkenes in a Z-selective manner. While TMSCF₂Br has been documented as the precursor of difluoro carbene, it exhibits another possibility in this transformation, a formal bromofluoro carbene surrogate. The alkenyl bromide unit of the products could directly engage in a variety of transformations.