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Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation.

ABSTRACT: A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The latter intermediates underwent SOMOphilic alkynylation by methanesulfonyl alkynes to afford internal alkynes upon loss of a sulfonyl radical. The effect of different radicofugal groups on the reaction outcome was evaluated and rationalized via a combined experimental and computational approach.

SUBMITTER: Capaldo L

PROVIDER: S-EPMC8041368 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation.

Capaldo Luca L Ravelli Davide D

Organic letters 20210303 6

A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The latter intermediates underwent SOMOphilic alkynylation by methanesulfonyl alkynes to afford internal alkynes upon loss of a sulfonyl radical. The effect of different radicofugal groups on the reaction outcome was evaluated and rationalized via a ...[more]

PMID: 33656899

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