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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.


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.

SUBMITTER: Scattolin T 

PROVIDER: S-EPMC6468269 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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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.

Scattolin Thomas T   Senol Erdem E   Yin Guoyin G   Guo Qianqian Q   Schoenebeck Franziska F  

Angewandte Chemie (International ed. in English) 20180820 38


This report widens the repertoire of emerging Pd<sup>I</sup> catalysis to carbon-heteroatom, that is, C-S bond formation. While Pd<sup>0</sup> -catalyzed protocols may suffer from the formation of poisonous sulfide-bound off-cycle intermediates and lack of selectivity, the mechanistically diverse Pd<sup>I</sup> 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 pres  ...[more]

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