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Transition-Metal-Free Hydrogenation of Aryl Halides: From Alcohol to Aldehyde

Hong-Xing Zheng, Xiang-Huan Shan, Jian-Ping Qu* and Yan-Biao Kang*

*Nanjing Tech University, Nanjing 211816; University of Science and Technology of China, Hefei 230026, China, Email: ias_jpqunjtech.edu.cn, ybkangustc.edu.cn

H.-X. Zheng, X.-H. Shan, J.-P. Qu, Y.-B. Kang, Org. Lett., 2017, 19, 5114-5117.

DOI: 10.1021/acs.orglett.7b02399 (free Supporting Information)


Abstract

A transition-metal- and catalyst-free hydrogenation of a wide range of aryl halides is promoted by bases using either aldehydes or alcohols as hydrogen source. One equivalent of benzaldehyde affords an equal yield as that of 0.5 equiv of benzyl alcohol. The kinetic study reveals that the initial rate of PhCHO is nearly 4 times faster than that of BnOH. Radical trapping experiments indicate the radical nature of this reaction.

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proposed mechanism



Key Words

dehalogenations, benzyl alcohol, benzaldehyde


ID: J54-Y2017