Deconstructing selectivity in the gold-promoted cyclization of alkynyl benzothioamides to six-membered mesoionic carbene or acyclic carbene complexes

Sai V. C. Vummaleti, Laura Falivene, Albert Poater, Luigi Cavallo

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

We demonstrate that the experimentally observed switch in selectivity from 5-exo-dig to 6-endo-dig cyclization of an alkynyl substrate, promoted by Au I and AuIII complexes, is connected to a switch from thermodynamic to kinetic reaction control. The AuIII center pushes alkyne coordination toward a single Au-C(alkyne) σ-bond, conferring carbocationic character (and reactivity) to the distal alkyne C atom. © 2014 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)1287-1291
Number of pages5
JournalACS Catalysis
Volume4
Issue number5
DOIs
StatePublished - Mar 27 2014

ASJC Scopus subject areas

  • Catalysis

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