4.8 Article

Gold(I)-Catalyzed Diazo Coupling: Strategy towards Alkene Formation and Tandem Benzannulation

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 41, Pages 11070-11074

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201406712

Keywords

annulations; alkenes; cross-coupling; diazo compounds; gold

Funding

  1. NSFC [21172023]
  2. Priority Academic Program Development of Jiangsu Higher Education Institution (PAPD)
  3. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]

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A gold(I)-catalyzed cross-coupling of diazo compounds to afford tetrasubstituted alkenes has been developed by taking advantage of a trivial electronic difference between two diazo substrates. A N-heterocyclic-carbene-derived gold complex is the most effective catalyst for this transformation. Based on this new strategy, a gold(I)-initiated benzannulation has been achieved through a tandem reaction involving a diazo cross-coupling, 6 pi electrocyclization, and oxidative aromatization.

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