Light-Induced Gold-Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Jin Xie, Kohei Sekine, Sina Witzel, Petra Krämer, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C−X (heteroatom) and C−C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.

Original languageEnglish
Pages (from-to)16648-16653
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number51
DOIs
Publication statusPublished - Dec 17 2018
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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