Samarium(II) Iodide-Promoted Intermolecular and Intramolecular Ketone-Nitrile Reductive Coupling Reactions

Longhu Zhou; Yongmin Zhang; Daqing Shi

doi:10.1055/s-2000-6220

Synthesis 2000; 2000(1): 91-98
DOI: 10.1055/s-2000-6220

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Samarium(II) Iodide-Promoted Intermolecular and Intramolecular Ketone-Nitrile Reductive Coupling Reactions

Longhu Zhou^* , Yongmin Zhang, Daqing Shi

^*Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou, 310028, P. R. China; Fax +86 (5 71) 8 27 38 02

Abstract

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Samarium(II) iodide, a strong one-electron transfer reducing reagent, has been successfully utilized for the intermolecular and intramolecular reductive coupling reactions of ketones with nitriles. α-Hydroxy ketones, monocyclic, fused bicyclic α-hydroxy ketones and monocyclic α-amino alcohols composed of a number of substitution patterns have been prepared in good yields at room temperature or reflux under neutral conditions. The procedure can avoid overreduction of the resulting of α-hydroxy ketones or α-amino alcohols. The crystal structures of monocyclic α-amino alcohols are reported.

samarium diiodide - ketone-nitrile - reductive coupling - cyclizations - α-ketols - α-amino alcohols - aldehydes - ketones - heterocycles

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