Abstract
Eight new pentavalent organobismuth derivatives were synthesized by the reactions of triphenylbismuth or phenyl-2,2"-biphenylenebismuth with chiral (1R)-(–)-camphor-10-sulfonic, (–)-menthyloxyacetic, or (R)-3-phenylbutyric acids. Enantioselective C-arylation of enolizable substrates with organobismuth reagents was carried out for the first time. Unlike iodine, sulfur, and selenium derivatives, which contain a five-membered heterocycle including the 2,2"-biphenylene fragment, phenyl-2,2"-biphenylene organobismuth analogs enter into C-arylation reactions accompanied by the selective transfer exclusively of the phenyl group to the organic substrate.
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Finet, JP., Fedorov, A.Y. Synthesis and reactivity of chiral pentavalent bismuth derivatives. Russian Chemical Bulletin 53, 1488–1495 (2004). https://doi.org/10.1023/B:RUCB.0000046245.89207.5c
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DOI: https://doi.org/10.1023/B:RUCB.0000046245.89207.5c
- C-arylation
- triphenylbismuth
- phenyl-2,2"-biphenylenebismuth
- enantioselectivity