Divergent Reaction of Isocyanides with -Bromobenzaldehydes: Synthesis of Ketenimines and Lactams with Isoindolinone Cores.

Org Lett

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, People's Republic of China.

Published: October 2021


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Article Abstract

A divergent reaction of isocyanides with -bromobenzaldehydes for the synthesis of isoindolinone-derived ketenimines and lactams was disclosed. The reaction features readily available reactants, relatively mild conditions, and high yields of products. Ketenimines could be applied in further transformations for access to other functional molecules. A mechanism study showed that the palladium-migration/imine-insertion process was the key step in this reaction.

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http://dx.doi.org/10.1021/acs.orglett.1c02422DOI Listing

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