4.8 Article

Visible-Light-Induced Multicomponent Synthesis of γ-Amino Esters with Diazo Compounds

Journal

ORGANIC LETTERS
Volume 23, Issue 16, Pages 6278-6282

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02071

Keywords

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Funding

  1. National Natural Science Foundation of China [21672047]
  2. State Key Laboratory of Urban Water Resource and Environment [2018DX02]
  3. Science and Technology Plan of Shenzhen [JCYJ20180306172044124]
  4. Natural Science Foundation of Guangdong [2020A1515010564]
  5. Shenzhen Government
  6. Guangdong Province Covid-19 Pandemic Control Research Fund [2020KZDZX1218]
  7. Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University

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A visible-light-induced multicomponent reaction of ethyl diazoacetate, diarylamines, and styrene-type alkenes has been developed as an efficient method for 1,2-difunctionalization of alkenes. The reaction proceeds through the generation of carbon-centered radicals from diazo compounds by a visible-light-promoted proton-coupled electron transfer process, leading to the formation of-N-amino esters.
A visible-light-induced multicomponent reaction of ethyl diazoacetate, diarylamines, and styrene-type alkenes is described. This novel 1,2-difunctionalization of alkenes can be readily achieved under a simple operation and mild conditions, affording.-amino esters as major products. The reaction proceeds through the generation of carbon-centered radicals from diazo compounds by a visible-light-promoted proton-coupled electron transfer (PCET) process. The carbon radicals then add to diverse alkenes, delivering new carbon radical species, and the final products are formed with N-centered radicals via a radical-radical coupling.

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