Functional Group Migration-Driven Quaternary Carbon Editing via Intramolecular [4+2] Annulation

Organic Letters 2026

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Authors: Yi-Xin Xing, Bo-Xi Liu, Feng C. Zhou, Syed Anis Ali Shah, Daopeng Sheng, Weidong Rao, Shu-Su Shen, Chen Hui Zhu, Shun‐Yi Wang
DOI: 10.1021/acs.orglett.6c02476
Cited by: 1
References: 87

Abstract

A photocatalytic tandem radical intramolecular [4+2] cyclization of unactivated cyanated alkenes for constructing functionalized benzo[1,6]naphthyridinones through the integration of radical cyano migration and hydrogen atom transfer (HAT) strategies is reported. This protocol uses mild reaction conditions, readily accessible and stable substrates, and a metal-free organic photocatalyst while enabling late-stage functionalization. The mechanistic study reveals that the intramolecular [4+2] cyclization mechanism involves radical addition to an unactivated alkene, followed by 1,4-cyano migration, 1,6-HAT, and a subsequent intramolecular 6-endo-trig radical cyclization process.

Fields of Study & Subjects

Radical Photochemical Reactions Catalytic C–H Functionalization Methods Photochromic and Fluorescence Chemistry

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
32
Pages
10187–10193
Publication date
31 July 2026
Language
EN