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Catalytic Staudinger Reduction at Room Temperature

Danny C. Lenstra, Joris J. Wolf, Jasmin Mecinović*

*Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, Odense 5230, Denmark, Email: mecinovicsdu.dk

D. C. Lenstra, J. J. Wolf, J. Mecinović, J. Org. Chem., 2019, 84, 6536-6545.

DOI: 10.1021/acs.joc.9b00831 (free Supporting Information)


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Abstract

An efficient catalytic Staudinger reduction at room temperature provides structurally diverse amines from azides in excellent yields in the presence of catalytic amounts of triphenylphosphine and diphenyldisiloxane as terminal reducing agent. The reaction exhibits high chemoselectivity and tolerates nitriles, alkenes, alkynes, esters, and ketones.

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Key Words

Staudinger Reduction, silanes, triphenylphosphine, organocatalysis


ID: J42-Y2019