Chemoselective Synthesis of α-Halo- α,α-difluoromethyl Ketones from Trimethyl(phenylethynyl)silane

Xiaoyan Bai; Yuye Bai; Ya Li; Cong Zhao; Hongxuan Du; Yibiao Li; Chengshuo Shen; Min Zhang; Lu Chen

doi:10.1021/acs.orglett.4c01365

Chemoselective Synthesis of α-Halo- α,α-difluoromethyl Ketones from Trimethyl(phenylethynyl)silane

Org Lett. 2024 May 31;26(21):4508-4513. doi: 10.1021/acs.orglett.4c01365. Epub 2024 May 21.

Authors

Xiaoyan Bai¹, Yuye Bai¹, Ya Li¹, Cong Zhao¹, Hongxuan Du¹, Yibiao Li¹, Chengshuo Shen², Min Zhang³, Lu Chen¹

Affiliations

¹ School of Environmental and Chemical Engineering, Wuyi University, Jiangmen 529020, P. R. China.
² Department of Chemistry, Zhejiang Sci-Tech University, Xiasha Campus, Hangzhou 310018, P. R. China.
³ Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Wushan Rd-381, Guangzhou 510641, P. R. China.

PMID: 38770840
DOI: 10.1021/acs.orglett.4c01365

Abstract

Here, we describe a novel strategy for chemoselective synthesis of α-halo-α,α-difluoromethyl ketones (-COCF₃ and -COClCF₂ motifs) from trimethyl(phenylethynyl)silane under catalyst-free and mild conditions. Commercially available Selectfluor or additional NaCl as halogen reagent was employed to complete this transformation, thereby demonstrating the potential synthetic value of this new reaction in organic synthesis.