Site-Selective C-S Bond Formation at C-Br over C-OTf and C-Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst

Angewandte Chemie
Thomas ScattolinFranziska Schoenebeck

Abstract

This report widens the repertoire of emerging PdI catalysis to carbon-heteroatom, that is, C-S bond formation. While Pd0 -catalyzed protocols may suffer from the formation of poisonous sulfide-bound off-cycle intermediates and lack of selectivity, the mechanistically diverse PdI catalysis concept circumvents these challenges and allows for C-S bond formation (S-aryl and S-alkyl) of a wide range of aryl halides. Site-selective thiolations of C-Br sites in the presence of C-Cl and C-OTf were achieved in a general and a priori predictable fashion. Computational, spectroscopic, X-ray, and reactivity data support dinuclear PdI catalysis to be operative. Contrary to air-sensitive Pd0 , the active PdI species was easily recovered in the open atmosphere and subjected to multiple rounds of recycling.

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Citations

Nov 2, 2018·Angewandte Chemie·Claudia J DiehlFranziska Schoenebeck
Mar 27, 2019·Chemistry : a European Journal·Erdem SenolFranziska Schoenebeck
Apr 16, 2020·Angewandte Chemie·Samir Bouayad-GervaisFranziska Schoenebeck
Sep 15, 2020·Chemical Communications : Chem Comm·Thomas ScattolinFabiano Visentin
Oct 23, 2018·Angewandte Chemie·Theresa SpergerFranziska Schoenebeck
Jun 14, 2019·Angewandte Chemie·Xiang-Yu ChenFranziska Schoenebeck
Oct 16, 2020·Angewandte Chemie·Christoph FrickeFranziska Schoenebeck
Nov 19, 2020·Chemistry : a European Journal·Emily K ReevesSharon R Neufeldt
Apr 3, 2020·Journal of the American Chemical Society·Frederik SandfortFrank Glorius
Jun 5, 2021·Organic Letters·Aymane Selmani, Franziska Schoenebeck
Dec 18, 2018·Organic Letters·Paul H GehrtzIvana Fleischer
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Jun 28, 2019·The Journal of Organic Chemistry·Xuanhe RenBingxin Yuan
Dec 11, 2020·The Journal of Organic Chemistry·Shimin XieJianyu Dong
Jun 4, 2020·Organic Letters·Aymane SelmaniFranziska Schoenebeck

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Methods Mentioned

BETA
NMR
column chromatography

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