Ir-Catalyzed Ortho-Selective C-H Borylation of Difluoromethyl Arenes

Chen-Yuan Li; Zengyu Zhang; Xiaoyu Yan

doi:10.1021/acs.orglett.3c02308

Ir-Catalyzed Ortho-Selective C-H Borylation of Difluoromethyl Arenes

Org Lett. 2023 Oct 13;25(40):7278-7282. doi: 10.1021/acs.orglett.3c02308. Epub 2023 Oct 2.

Authors

Chen-Yuan Li¹, Zengyu Zhang¹, Xiaoyu Yan¹

Affiliation

¹ Key Laboratory of Advanced Light Conversion Materials and Biophotonics, Department of Chemistry, Renmin University of China, Beijing 100872, China.

PMID: 37782225
DOI: 10.1021/acs.orglett.3c02308

Abstract

The difluoromethyl group (CF₂H) has received great attention due to its distinct properties in recent years. Herein, we report a new strategy for postmodification of difluoromethyl compounds. Ortho-selective C-H borylation of difluoromethyl arenes is achieved by a cyclometalated mesoionic carbene-Ir complex. The regioselectivity is controlled by a hydrogen bond between CF₂H and the boryl group via the outer-sphere direction.