Mechanistic Insights on the Hydration of Terminal and Internal Allenes Catalyzed by [(NHC)Au]+

Sara Muñoz-López, Almudena Couce-Rios, Giuseppe Sciortino, Agustí Lledós, Gregori Ujaque

Research output: Contribution to journalArticleResearch

4 Citations (Scopus)

Abstract

© 2018 American Chemical Society. The reaction mechanism for the hydration of internal and terminal allenes catalyzed by [Au(NHC)]+ is analyzed by means of DFT calculations. Several reaction pathways for generating the two possible regioisomers were evaluated. Direct addition on coordinated allenes or to an intermediate with a σ-allylic cation structure as suggested for the Au(I)-catalyzed hydroamination of allenes were considered. The isomerization between both regioisomeric products catalyzed by the same Au(I) catalyst was also investigated as suggested for hydroalkoxylation of allenes. The regioselectivity of the reaction predicted by computation agrees with experiment for both terminal and internal allenes. The presence of alkyl or aryl substituents introduces differences in the reaction mechanism for the hydration process.
Original languageEnglish
Pages (from-to)3543-3551
JournalOrganometallics
Volume37
DOIs
Publication statusPublished - 22 Oct 2018

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