A ligand-enabled metallaphotoredox protocol for Suzuki-Miyaura cross-couplings for the synthesis of diarylmethanes

Jianbin Li; Chia-Yu Huang; Chao-Jun Li

doi:10.1016/j.xpro.2022.101618

A ligand-enabled metallaphotoredox protocol for Suzuki-Miyaura cross-couplings for the synthesis of diarylmethanes

STAR Protoc. 2022 Aug 18;3(3):101618. doi: 10.1016/j.xpro.2022.101618. eCollection 2022 Sep 16.

Authors

Jianbin Li¹, Chia-Yu Huang¹, Chao-Jun Li²

Affiliations

¹ Department of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street W., Montreal, QC H3A 0B8, Canada.
² Department of Chemistry, FRQNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street W., Montreal, QC H3A 0B8, Canada. Electronic address: cj.li@mcgill.ca.

Abstract

Here, we present a ligand-enabled metallaphotoredox Suzuki-Miyaura cross-coupling protocol for the facile synthesis of diarylmethanes. Specifically, we describe the preparation of a unique class of ligands, 2,4-diarylquinolines, and demonstrate their application in nickel-catalyzed fragment couplings between alkyltrifluoroborates and haloarenes. We detail the synthesis of the most enabling ligand, PPQN^2,4-di-OMe, on a gram scale via sequential Grignard reaction and Friedländer condensation. We also outline how coupling reactions are performed without external photocatalysts under violet light irradiation. For complete details on the use and execution of this protocol, please refer to Li et al. (2022b).

Keywords: Chemistry; Energy.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Ligands
Nickel*

Substances

Ligands
Nickel