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Published on: April 4, 2014
Ti-Catalyzed Dehydroxylation of Tertiary Alcohols
Quan Lin1,2, Weiqi Tong3, Xing-Zhong Shu4
1School of Materials Science and Engineering, Shanghai University, 99 Shangda Road, Shanghai 200444, People's Republic of China.
Abstract:
Herein we report a Ti-catalyzed direct dehydroxylation of tertiary aliphatic alcohols under mild reaction conditions, forging Barton-type deoxygenation products. This protocol tolerates a wide range of functional groups, including primary alkyl chloride and carbonyl groups. It allows for selective dehydroxylation of tertiary alcohols in diols and the formation of deuterated products with moderate deuterium incorporation. The efficient modification of several drugs and natural products (or their derivatives) highlights the synthetic utility of this method.
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