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Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane

Smith, Clive A. and Cross, Laura E. and Hughes, Kimberley and Davis, Rebecca E. and Judd, Duncan B. and Merritt, Andrew T. (2009) Direct reductive aminations with catalytic molybdenum dioxide dichloride and phenylsilane. Tetrahedron Letters, 50 (34). pp. 4906-4911. ISSN 0040-4039

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Abstract

A powerful direct reductive amination (DRA) method is developed, using catalytic MoO2Cl2 and phenylsilane (PhSiH3) as the reducing agent. The alkylation of a range of amines (pK(a) 0-7.8) with both an electron-deficient and two electron-rich-aldehydes is achieved in good to excellent yields. The novel employment of this DRA in alcoholic solvents significantly improves the reaction scope and excellent functional group selectivity is exhibited.