K3PO4-Promoted Cascade Annulation of ortho -Hydroxyphenyl-Substituted para -Quinone Methides and Vinylsulfonium Salts: An Access to 2 H -Chromenes

Abstract The compounds containing 2H-chromene scaffolds exhibit a broad spectrum of biological and pharmaceutical activities. Herein, a novel metal-free reaction of ortho-hydroxyphenyl-substituted p-QMs with vinylsulfonium salts has successfully been developed, leading to the formation of 2H-chromenes in a one-pot way, of which 2H-chromenes themselves could also be easily further transformed into valuable ring-contraction products, benzofurans, via a rearrangement strategy under mild conditions. The protocol circumvents several limitations of prior methods, including the use of transition metals (Pd, Co, Ag, Ni, etc.), equivalent levels of special agents, expensive ligands, the requirement of difficult-to-access starting materials, and harsh reaction environments.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-11-03
DOI
https://doi.org/10.1021/acs.joc.6c01886
Primary Topic
Organic Chemistry Synthesis Methods
Type
article
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article

K3PO4-Promoted Cascade Annulation of ortho -Hydroxyphenyl-Substituted para -Quinone Methides and Vinylsulfonium Salts: An Access to 2 H -Chromenes

Weiyin Yi, Qingwei Wang, Yuxi Wang, qiurou yu et al.
The Journal of Organic Chemistry
Organic Chemistry Synthesis Methods
article

K3PO4-Promoted Cascade Annulation of ortho -Hydroxyphenyl-Substituted para -Quinone Methides and Vinylsulfonium Salts: An Access to 2 H -Chromenes

Weiyin Yi, Qingwei Wang, Yuxi Wang, qiurou yu, Jiaping Feng, Wen Cheng
article en

Abstract

Abstract The compounds containing 2H-chromene scaffolds exhibit a broad spectrum of biological and pharmaceutical activities. Herein, a novel metal-free reaction of ortho-hydroxyphenyl-substituted p-QMs with vinylsulfonium salts has successfully been developed, leading to the formation of 2H-chromenes in a one-pot way, of which 2H-chromenes themselves could also be easily further transformed into valuable ring-contraction products, benzofurans, via a rearrangement strategy under mild conditions. The protocol circumvents several limitations of prior methods, including the use of transition metals (Pd, Co, Ag, Ni, etc.), equivalent levels of special agents, expensive ligands, the requirement of difficult-to-access starting materials, and harsh reaction environments.

The Journal of Organic Chemistry
Shanghai Institute of Technology (CN)
Openalex Percentile: Top 27%
Organic Chemistry Synthesis Methods
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K3PO4-Promoted Cascade Annulation of ortho -Hydroxyphenyl-Substituted para -Quinone Methides and Vinylsulfonium Salts: An Access to 2 H -Chromenes — Weiyin Yi, Qingwei Wang, et al. · The Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS