Visible light-mediated metal-free alkyl Suzuki-Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives

Chuan Hua Qu, Xiao Yan, Shu Ting Li, Jian Bo Liu, Zhi Gang Xu, Zhong Zhu Chen, Dian Yong Tang, Huan Xiang Liu, Gui Ting Song

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The Suzuki-Miyaura reaction has greatly facilitated the construction of C-C bonds and is well appreciated in medicinal chemistry, yet transition metal residues in this process are an unavoidable challenge. Herein, we report the first visible-light-driven photocatalyst-free coupling reaction of alkenylboronic acids/esters with α-bromodifluoroacylarenes, providing streamlining access to a series of Suzuki coupling products. The reactions proceed under metal-free conditions with a wide substrate scope. Mechanistic experiments and DFT calculation studies revealed that halogen bonding interactions, mainly generated in situ between α-bromodifluoroacylarenes and tertiary amines, could promote the Csp3-Br bond homolytic cleavage from difluorobromoaryl ketones.

Original languageEnglish
Pages (from-to)3453-3461
Number of pages9
JournalGreen Chemistry
Volume25
Issue number9
DOIs
Publication statusPublished - 13 Apr 2023

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