Selective Three-Component 1,2-Aminoalkoxylation of 1-Aryl-1,3-dienes by Dual Photoredox and Copper Catalysis.

Org Lett

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.

Published: October 2022

AI Article Synopsis

  • A new method for a 1,2-aminooxygenation reaction of 1,3-dienes uses dual photoredox and copper catalysis, making the process more effective.* -
  • The reaction employs -aminopyridinium salts as sources of N-centered radicals and nucleophilic alcohols for oxygen, yielding 1,2-aminoalkoxylation products efficiently.* -
  • Initial studies indicate that the reaction works through radical intermediates, supporting the proposed mechanism of the reaction.*

Article Abstract

A three-component 1,2-aminooxygenation reaction of 1,3-dienes by dual photoredox and copper catalysis is described. This protocol uses -aminopyridinium salts as N-centered radical precursors and nucleophilic alcohols as oxygen sources, providing modular and practical access to 1,2-aminoalkoxylation products with good yields and regioselectivity. Preliminary mechanistic studies support the radical property of the reaction and the involvement of N-centered radical intermediates.

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Source
http://dx.doi.org/10.1021/acs.orglett.2c03124DOI Listing

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