Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis

Manuel Pérez, Christopher B. Caputo, Roman Dobrovetsky, Douglas W. Stephan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [(C 6F5)3PF][B(C6F5) 4] 1 is shown to catalyze the dehydrocoupling of silanes with amines, thiols, phenols, and carboxylic acids to form the Si-E bond (E = N, S, O) with the liberation of H2 (21 examples). This catalysis, when performed in the presence of a series of olefins, yields the concurrent formation of the products of dehydrocoupling and transfer hydrogenation of the olefin (30 examples). This reactivity provides a strategy for metal-free catalysis of olefin hydrogenations. The mechanisms for both catalytic reactions are proposed and supported by experiment and density functional theory calculations.

Original languageEnglish
Pages (from-to)10917-10921
Number of pages5
JournalProceedings of the National Academy of Sciences of the United States of America
Volume111
Issue number30
DOIs
StatePublished - 2014
Externally publishedYes

Funding

FundersFunder number
Natural Sciences and Engineering Research Council of Canada

    Keywords

    • Fluorophosphonium

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