Palladium-Catalyzed Direct Selanylation of Chalcogenophenes and Arenes Assisted by 2-(Methylthio)amide
Gul Badshaha, Carla M. B. Gomesa, Sher Alib, Eduardo Q. Luza, Gabriel L. Silvérioa, Francielli S. Santanac, Diego Secklera, Douglas Bernardo Paixãod, Paulo H. Schneiderd, Daniel S. Rampona✉
- aLaboratory of Polymers and Catalysis(LaPoCa),Department of Chemistry, Federal University of Paraná, P.O. Box 19061, Curitiba 81531-980, Paraná, Brazil
- bFaculty of Animal Science and Food Engineering, University of São Paulo, Pirassununga 13635-900, São Paulo, Brazil
- cDepartment of Chemistry, Federal University of Paraná, P.O. Box 19061, Curitiba 81531-990, Paraná, Brazil
- dInstituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio Grande do Sul (UFRGS), Porto Alegre 91501-970, Rio Grande do Sul, Brazil
- ✉Corresponding author
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Abstract
The direct and selective conversion of a C-H bond into a C-Se bond remains a significant challenge, which is even more intricate with substrates having an innate regioselectivity under several reaction conditions, such as chalcogenophenes. We overrode their selectivity toward selanylation using palladium, copper, and the 2-(methylthio)amide directing group. This chelation-assisted direct selanylation was also suitable for mono and double ortho functionalization of arenes. The mechanistic studies indicate high-valent Pd(IV) species in the catalytic cycle, a reversible C-H activation step, and Cu(II) as a sequestering agent for organoselenide byproducts.
TL;DRChelation-assisted direct selanylation was also suitable for mono and double ortho functionalization of arenes and high-valent Pd(IV) species in the catalytic cycle, a reversible C-H activation step, and Cu(II) as a sequestering agent for organoselenide byproducts. (Semantic Scholar)