Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 26, Pages 11382-11387Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c05343
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Funding
- Max-Planck-Gesellschaft
- Max-Planck-Institut fur Kohlenforschung
- Fonds der Chemischen Industrie (FCI-VCI)
- European Union [850496, 833361]
- Marie Curie Actions (MSCA) [833361] Funding Source: Marie Curie Actions (MSCA)
- European Research Council (ERC) [850496] Funding Source: European Research Council (ERC)
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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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