Copper-Catalyzed Oxidative Cyclization/1,2-Amino Migration Cascade Reaction.

Org Lett

Key Laboratory of Synthetic and Nature Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science , Northwest University, Xi'an 710127 , P. R. China.

Published: May 2018

AI Article Synopsis

  • A new copper-catalyzed reaction has been created for efficiently synthesizing substituted pyrroles from enamino esters through a combined oxidative cyclization and amino migration process.
  • The reaction involves breaking one C-N bond while forming two new C-N bonds and one C(sp)-C(sp) bond in a single step, showcasing its efficiency.
  • It operates under mild conditions, uses oxygen as the oxidant, and works well with various functional groups, producing valuable aminomethyl-substituted pyrroles with good yields.

Article Abstract

A novel and efficient copper-catalyzed tandem oxidative cyclization/1,2-amino migration of readily available enamino esters for the synthesis of substituted pyrroles has been developed. In this reaction, one C-N bond was cleaved, and two new C-N bonds and one C(sp)-C(sp) bond were constructed in one pot. This catalytic system has the obvious advantages of mild reaction conditions and the use of oxygen as the oxidant. The reaction tolerates a wide range of functional groups and is a reliable method for the straightforward synthesis of valuable aminomethyl-substituted pyrroles in good yields.

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Source
http://dx.doi.org/10.1021/acs.orglett.8b01139DOI Listing

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