4.7 Article

Catalytic Cross-Coupling of Vinyl Golds with Diazonium Salts under Photoredox and Thermal Conditions

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 12, Pages 2622-2628

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500525

Keywords

cross-coupling; diazonium salts; gold catalysis; radical chain reaction; visible light photocatalysis

Funding

  1. National Research Foundation of Korea [NRF-2012M3A7B4049653, NRF-2014-011165]
  2. National Research Foundation of Korea [2014R1A5A1011165, 2012M3A7B4049653] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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Catalytically generated vinyl gold complexes from tert-butyl allenoates were found to undergo an efficient cross-coupling with arenediazonium salts. The gold(I)-gold(III) redox cycle can be accessed under two different conditions, i.e., visible-light photoredox as well as a thermally induced radical chain pathway. The current C(sp(2))-C(sp(2)) cross-coupling protocol that is catalytic in gold, would make available desirable structural diversity to the traditional cross-coupling chemistry.

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