Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

Miao Wang; Chau Ming So

doi:10.1021/acs.orglett.1c04138

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

Org Lett. 2022 Jan 21;24(2):681-685. doi: 10.1021/acs.orglett.1c04138. Epub 2022 Jan 3.

Authors

Miao Wang^{1

2}, Chau Ming So^{1

3}

Affiliations

¹ State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
² Henan Key Laboratory of Function-Oriented Porous Materials, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, P. R. China.
³ The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen 518057, People's Republic of China.

PMID: 34978819
DOI: 10.1021/acs.orglett.1c04138

Abstract

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C-Br > C-Cl > C-OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki-Miyaura coupling reactions.

Publication types

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