A chemoselective polarity-mismatched photocatalytic C(sp3)–C(sp2) cross-coupling enabled by synergistic boron activation

Jeremy Brals, Thomas McGuire, Allan J. B. Watson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
7 Downloads (Pure)

Abstract

We report the development of a C(sp3)–C(sp2) coupling reaction using styrene boronic acids and redox-active esters under photoredox catalysis. The reaction proceeds through an unusual polarity-mismatched radical addition mechanism that is orthogonal to established processes. Synergistic activation of the radical precursor and organoboron are critical mechanistic events. Activation of an N-hydroxyphthalimide (NHPI) ester by coordination to boron enables electron transfer, with decomposition leading to a nucleofuge rebound, activating the organoboron to radical addition. The unique mechanism enables chemoselective coupling of styrene boronic acids in the presence of other alkene radical acceptors. The scope and limitations of the reaction, and a detailed mechanistic investigation are presented.
Original languageEnglish
Article numbere202310462
Number of pages9
JournalAngewandte Chemie International Edition
Volume62
Issue number42
Early online date13 Sept 2023
DOIs
Publication statusPublished - 9 Oct 2023

Keywords

  • Boron
  • Chemoselectivity
  • Cross-coupling
  • Crossover
  • Photosynthesis

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