Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 7, Pages 1810-1814Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611058
Keywords
boronic esters; cross-coupling; furans; stereospecificity; trifluoromethylation
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Funding
- Horizon's Marie Sklodowska-Curie [EMTECS/652890]
- EPSRC [EP/I038071/1]
- University of Bristol
- EPSRC [EP/K03927X/1, EP/I038071/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1, EP/I038071/1] Funding Source: researchfish
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In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.
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