Synthetic Communications

Unexpected Transformation of Aldehydes into Benzoins with Copper (I)/Samarium

Y Liu, H Wang, Y Fu, Y Qi, K Yang

Index: Liu, Yongjun; Wang, Hui; Fu, Yulong; Qi, Yan; Yang, Kuiwei Synthetic Communications, 2014 , vol. 44, # 2 p. 259 - 266

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Abstract

The reductive coupling of aldehydes to afford pinacolic alcohols using all kinds of reducing agents involving samarium is well known. In this report, however, treatment of aromatic aldehydes with Cu(I)/Sm system produces benoins and/or benzils in good yields. A possible mechanism is proposed where Cu(I) not only activates the Sm metal but also promotes the dehydrogenation of the intermediates, during which a Cu(III) species may be involved.