Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts | Zendy

Oriol Planas | Zendy; Vytautas Pečiukėnas | Zendy; Josep Cornellà | Zendy

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Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Author(s) -

Oriol Planas,

Vytautas Pečiukėnas,

Josep Cornellà

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c05343

Subject(s) - chemistry , trifluoromethanesulfonate , electrophile , sulfonate , bismuth , catalysis , ligand (biochemistry) , oxidative coupling of methane , combinatorial chemistry , catalytic cycle , sulfone , coupling (piping) , medicinal chemistry , organic chemistry , sodium , receptor , mechanical engineering , biochemistry , engineering

Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp 2 )-O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.

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