Gold(I)-catalyzed intermolecular hydroalkoxylation of allenes: A DFT study

Robert S. Paton, Feliu Maseras

Research output: Contribution to journalArticleResearchpeer-review

104 Citations (Scopus)

Abstract

The mechanistic and regiochemical aspects in the Au(I)-catalyzed intermolecular hydroalkoxylation of allenes have been studied computationally. The most favorable pathway is nucleophilic attack of an Au(I)-coordinated allene, which occurs irreversibly. An Au(I)-catalyzed mechanism is proposed that allows the facile interconversion of regioisomeric allylic ether products. The regioisomers are connected via a stabilized diether intermediate with a C-Au σ-bond, which successfully explains the observed regioselectivity for the thermodynamic product. © 2009 American Chemical Society.
Original languageEnglish
Pages (from-to)2237-2240
JournalOrganic Letters
Volume11
Issue number11
DOIs
Publication statusPublished - 4 Jun 2009

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