Synlett 2019; 30(17): 1977-1980
DOI: 10.1055/s-0039-1690026
cluster
© Georg Thieme Verlag Stuttgart · New York

Transfer Hydration of Dinitriles to Dicarboxamides

Asuka Naraoka
a   Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
b   Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan   Email: h_naka@nagoya-u.jp
› Author Affiliations

H.N. is grateful for financial support from the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Number JP17K05859) and Toyota Physical and Chemical Research Institute (Toyota Riken).
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Publication History

Received: 30 June 2019

Accepted after revision: 04 September 2019

Publication Date:
24 September 2019 (online)


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Published as part of the Cluster Metathesis beyond Olefins

Abstract

We present a robust method for double transfer hydration of dinitriles to afford diamides. The transfer hydration of 1,n-dinitriles (n = 1–6) proceeds smoothly in the presence of a palladium(II) catalyst with acetamide as a water donor, affording the corresponding diamides in moderate to high yields, without involving significant side reactions such as monohydration or cyclization. The equilibrium was shifted in the forward direction by removing coproduced acetonitrile under reduced pressure.

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