ChemistrySelect 2018-03-30

An Efficient Protocol for the Synthesis of Primary Amides via Rh‐Catalyzed Rearrangement of Aldoximes

Fen Xu; Yuan‐Yuan Song; Yan‐Jie Li; Er‐Long Li; Xin‐Ran Wang; Wen‐Yue Li; Chun‐Sen Liu

Index: 10.1002/slct.201800265

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Abstract

A system consisting of catalytic amounts of [Rh(CH2=CH2)Cl]2/PPh2Cy, and PhCl as the solvent efficiently catalyzes selective rearrangement of aldoximes to furnish various primary amides in moderate to good yields. Replacing the [Rh(CH2=CH2)Cl]2 with Rh(NBD)2OTf enables the superior transformation to afford the amides with up to 99% yields. Attractive synthetic features associated with this methodology include absence of co‐catalysts, broad functional group tolerance, good to excellent yields, low metal loadings, and operational convenience.

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