Gold(I)‐Catalyzed Addition of Silylacetylenes to Acylsilanes: Synthesis of Indanones by CH Functionalization through a Gold(I) Carbenoid | Zendy

González Jairo | Zendy; Santamaría Javier | Zendy; Ballesteros Alfredo | Zendy

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Gold(I)‐Catalyzed Addition of Silylacetylenes to Acylsilanes: Synthesis of Indanones by CH Functionalization through a Gold(I) Carbenoid

Author(s) -

González Jairo,

Santamaría Javier,

Ballesteros Alfredo

Publication year - 2015

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201505830

Subject(s) - carbenoid , alkyne , acetylide , silylation , chemistry , surface modification , catalysis , combinatorial chemistry , photochemistry , organic chemistry , rhodium

A gold(I)‐catalyzed synthesis of indanones from trimethylsilylacetylenes and acylsilanes is presented. The reaction is initiated through a synergistic acylsilane activation–gold acetylide formation and involves consecutive alkyne σ‐gold(I) addition, π‐activation, and 1,2‐migration of a silyl group. Studies performed on the reaction mechanism allowed to establish the nature of the silyl migrating group and invoke the participation of a gold(I) carbenoid intermediate. The reaction is completed by a gold(I) CH functionalization step.

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