Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 6, Pages 947-957Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500743
Keywords
arylation; Barbier-Grignard-type reaction; cross-coupling; ketones; unactivated bromides
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Funding
- National Natural Science Foundation of China [21276104]
- Fundamental Research Funds for the Central Universities [21612403]
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A novel, highly versatile and efficient method has been developed for the Barbier-Grignard-type arylation of ketones and an unexpected cross-coupling of phenolic ketones was observed using unactivated bromides and magnesium in tetra-hydrofuran/toluene at 96 degrees C promoted by multicatalysts of cupric bromide (15 mol%), bismuth chloride (5 mol%) and silver bromide (10 mol%). The substituent and electronic effects on the reaction have been discussed. High yields of arylation and cross-coupling have been attained under mild conditions. A novel reasonable mechanism involving a quinone intermediate is proposed. The high chemical selectivity in the cross-coupling to the hydroxy group of phenolic ketones should help ketones find new applications.
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