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.

Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation / Capaldo, L; Ravelli, D. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 23:6(2021), pp. 2243-2247. [10.1021/acs.orglett.1c00381]

Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation

capaldo l;ravelli d
2021-01-01

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.
2021
Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation / Capaldo, L; Ravelli, D. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 23:6(2021), pp. 2243-2247. [10.1021/acs.orglett.1c00381]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2961105
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