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

Journal of the American Chemical Society
Oriol PlanasJosep Cornella

Abstract

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(sp2)-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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Citations

Jan 20, 2021·Journal of the American Chemical Society·Jeffrey M LipshultzAlexander T Radosevich
Apr 17, 2021·Chemical Communications : Chem Comm·Crispin Lichtenberg
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Agnieszka Adamczyk-WoźniakAndrzej Sporzyński
Jun 8, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Shigeru ShimadaMing Bao
Nov 5, 2020·Journal of the American Chemical Society·Yue PangJosep Cornella
Sep 3, 2021·Chemistry : a European Journal·Luca DemontiNoel Nebra
Nov 2, 2021·Journal of the American Chemical Society·Hayato FujimotoMamoru Tobisu
Dec 17, 2021·Journal of the American Chemical Society·Marc Magre, Josep Cornella

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Methods Mentioned

BETA
NMR

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