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April 25, 2026Organic Letters0 citations

Photocatalytic Regioselective Four-Component 1,4-Aryl Migration of N -Allylbenzamides To Access β-Arylethylamines

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CZCong-Hui ZhanHXHao XuYLY Li

Key Points

  • This research aims to develop a photocatalytic method for the regioselective synthesis of β-(hetero)arylethylamines.
  • Employs a four-component reaction involving N-allylbenzamides and aryl thianthrenium salts
  • Utilizes commercially available alcohols and DABCO·(SO2)2 under mild conditions
  • Demonstrates broad tolerability for various aryl groups with diverse substitution patterns
  • Achieves high regioselectivity in the synthesis of functionalized β-(hetero)arylethylamines
  • Reactions proceed smoothly under mild conditions with diverse aryl groups
  • Effectively constructs novel molecular frameworks through radical-mediated rearrangement

Abstract

Radical-mediated rearrangement reactions serve as a powerful strategy for the construction of novel molecular frameworks. Herein, we report a photochemical four-component 1,4-aryl migration protocol for the highly regioselective synthesis of functionalized β-(hetero)arylethylamines. This practical approach employs readily accessible N-allylbenzamides and aryl thianthrenium salts, along with commercially available alcohols and (DABCO)·(SO2)2 (DABSO) as starting materials, and proceeds smoothly under mild reaction conditions. Moreover, this method tolerates a wide range of migratory aryl groups bearing diverse substitution patterns and electronic properties.

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Cite This Study

Zhan et al. (2026) studied this question.

synapsesocial.com/papers/69ec5ac988ba6daa22dac564https://doi.org/10.1021/acs.orglett.6c01370
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