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En Route to a Practical Primary Alcohol Deoxygenation

Xi-Jie Dai and Chao-Jun Li*

*Department of Chemistry and FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbooke Street West, Montreal, Quebec H3A 0B8, Canada, Email: cj.limcgill.ca

X.-J. Dai, C.-J. Li, J. Am. Chem. Soc., 2016, 138, 5344-5440.

DOI: 10.1021/jacs.6b02344 (free Supporting Information)



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Abstract

Whereas an Ir-catalyzed alcohol deoxygenation on basis of dehydrogenation/Wolff-Kishner reduction is efficient mainly with activated alcohols under harsh reaction conditions, a Ru-catalyzed aliphatic primary alcohol deoxygenation offers good functional group tolerance and excellent efficiency under practical reaction conditions. Its synthetic utility is further illustrated by complete chemo- and regio-selectivity in complex molecular settings.

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proposed catalytic cycle



Key Words

deoxygenation, Wolff-Kishner reduction, hydrazine


ID: J48-Y2016