Radical Functionalization of 1, 6-Diene via Transannular Cyano Migration: Synthesis of Polysubstituted Cyclopentanes

Ziqiang Wang; Yasu Chen; Chen Zhu

doi:10.1002/cjoc.202401072

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (4) : 437 -442. DOI: 10.1002/cjoc.202401072

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Radical Functionalization of 1, 6-Diene via Transannular Cyano Migration: Synthesis of Polysubstituted Cyclopentanes

Ziqiang Wang ¹^,²
, Yasu Chen ¹
, Chen Zhu ¹^,²^,^†

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Abstract

An efficient transannular cyano migration is reported for gem-dicyano-1, 6-diene, which is triggered by the addition of external arylsulfonyl radicals. The overall transformation proceeds through a sequence of intramolecular 5-exo-trig cyclization, suprafacial 1, 4-cyano migration, and the capture by H or D atom, leading to the production of valuable polysubstituted cyclopentanes under mild photoredox catalytic conditions. The reaction is adapted to a wide range of sodium (hetero)arylsulfinates, demonstrating good functional group compatibility. This method provides a new protocol for radical-mediated functional group migration.

Keywords

Cyano migration / Cyclopentane / 1, 6-Diene / Photoredox catalysis / Radical reactions / Radicals / Cyclization / Rearrangement

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Ziqiang Wang, Yasu Chen, Chen Zhu. Radical Functionalization of 1, 6-Diene via Transannular Cyano Migration: Synthesis of Polysubstituted Cyclopentanes. Chinese Journal of Chemistry, 2025, 43(4): 437-442 DOI:10.1002/cjoc.202401072