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Communication | Special issue | Vol 80, No. 1, 2010, pp.163-168
Published online, 31st August, 2009
DOI: 10.3987/COM-09-S(S)42
Rhodium-Catalyzed 1,2-Addition of Sb-Phenyl-1,5-azastibocines to Functionalized Aldehydes

Naoki Kakusawa, Shuji Yasuike, and Jyoji Kurita*

*Faculty of Pharmaceutical Sciences, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Simple and efficient addition of a phenyl group to aldehydes was accomplished by the rhodium-catalyzed reaction of Sb-phenyl-1,5-azastibocines. Because of the soft nucleophilic character of 1,5-azastibocines, arylation of functionalized aldehydes having ketone, ester, and halogen moieties can be achieved to afford aryl alcohols. The reaction can be carried out under aerobic conditions, in striking contrast to the reactions with hard nucleophiles such as organolithium and Grignard reagents.