Catalyst-Free C(sp2)-H Borylation through Aryl Radical Generation from Thiophenium Salts via Electron Donor-Acceptor Complex Formation

Bo Li, Ke Wang, Huifeng Yue, Alwin Drichel, Jingjing Lin, Zhenying Su, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Aryl borates lie at the heart of carbon-carbon bond couplings, and they are widely applied to the synthesis of functional materials, pharmaceutical compounds, and natural products. Currently, synthetic methods for aryl borates are mostly limited to metal-catalyzed routes, and nonmetallic strategies remain comparatively underdeveloped. Herein, we report a mild, scalable, visible-light-induced cross-coupling between aryl dibenzothiophenium triflate salts and bis(catecholato)-diboron for the construction of C-B bonds in the absence of base, transition metal-ligand complex, or photoredox catalyst. Mechanistic studies reveal that this transformation is achieved through an electron donor-acceptor (EDA) complex activation in the absence of a catalyst. The mild reaction conditions allow the preparation of aromatic borates in good yields with excellent functional group tolerance. This photochemical protocol was also successfully applied to the late-stage modification of natural products and the synthesis of a drug intermediate, greatly demonstrating broadened utility.

Original languageEnglish (US)
Pages (from-to)7434-7439
Number of pages6
JournalOrganic Letters
Volume24
Issue number40
DOIs
StatePublished - Oct 14 2022

Bibliographical note

Funding Information:
B.L. acknowledges the China Scholarship Council for supporting this work.

Publisher Copyright:
© 2022 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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