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May 9, 2026The Journal of Organic Chemistry0 citations

Light-Induced Site-Selective Functionalization of Tertiary C(sp 3 )–H Bonds via a Synergistic System Combining TBADT with a Thiol Catalyst

WXWenbin XuPrinceton University JWJiajun WangJilin Normal University LYLiying YuJilin University of Chemical Technology

Key Points

The aim is to achieve site-selective functionalization of tertiary C(sp3)–H bonds using light.
Used electrophilic alkenes and alkynes for functionalization
Combined tetrabutylammonium decatungstate (TBADT) as a hydrogen atom abstractor with a thiol catalyst
Achieved the process under light irradiation with over 20:1 site selectivity
Achieved yields of up to 84%
Demonstrated greater than 20:1 site selectivity in functionalization
Reduced excess use of substrates significantly

Abstract

A site-selective functionalization of C(sp3)–H bonds is described. Electrophilic alkenes and alkynes are used to perform the site-selective functionalization of tertiary C(sp3)–H bonds enabled by merging a tetrabutylammonium decatungstate (TBADT) as a hydrogen atom abstractor (HAA) and a thiol as a hydrogen atom donator (HAD) under light irradiation. Excess use of substrates could be avoided; greater than 20:1 site selectivity and up to 84% yield could be obtained with the help of 2,4,6-tri-tert-butylbenzenethiol.

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Xu et al. (Thu,) studied this question.

synapsesocial.com/papers/69fed0abb9154b0b82877bfe https://doi.org/https://doi.org/10.1021/acs.joc.6c00460

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