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Acceptor-Controlled Transfer Dehydration of Amides to Nitriles

Hiroyuki Okabe, Asuka Naraoka, Takahiro Isogawa, Shunsuke Oishi, Hiroshi Naka*

*Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan, Email:

H. Okabe, A. Naraoka, T. Isogawa, S. Oishi, H. Naka, Org. Lett., 2019, 21, 4767-4770.

DOI: 10.1021/acs.orglett.9b01657

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Palladium-catalyzed dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions in the presence of dichloroacetonitrile as a water acceptor. Dichloroacetonitrile preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst.

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proposed mechanism

Key Words


ID: J54-Y2019