Visible-Light-Induced Radical-Cascade Brominative/Spirocyclization of Biaryl Ynones and CBr4: Synthesis of Spiro[5.5]trienones without External Additives

Abstract A visible-light-induced brominative spirocyclization of biaryl ynones with CBr4 for the synthesis of spiro[5.5]trienones is reported here. This protocol also features broad functional group tolerance and operational simplicity and achieves moderate to excellent yields as well as sustainable photocatalyst- and additive-free reaction conditions at room temperature under air. This strategy thus provides a green and practical synthetic avenue to access spiro[5.5]trienone scaffolds, and the resulting products exhibit diverse synthetic versatility for subsequent structural modifications.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-09-09
DOI
https://doi.org/10.1021/acs.joc.6c00985
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Visible-Light-Induced Radical-Cascade Brominative/Spirocyclization of Biaryl Ynones and CBr4: Synthesis of Spiro[5.5]trienones without External Additives

Tianyu Long, Qing‐Qing Yang, Long Wang, Han‐Han Kong et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Visible-Light-Induced Radical-Cascade Brominative/Spirocyclization of Biaryl Ynones and CBr4: Synthesis of Spiro[5.5]trienones without External Additives

Tianyu Long, Qing‐Qing Yang, Long Wang, Han‐Han Kong, Ge-Feng Long, Zheng-Wei Wu
article en

Abstract

Abstract A visible-light-induced brominative spirocyclization of biaryl ynones with CBr4 for the synthesis of spiro[5.5]trienones is reported here. This protocol also features broad functional group tolerance and operational simplicity and achieves moderate to excellent yields as well as sustainable photocatalyst- and additive-free reaction conditions at room temperature under air. This strategy thus provides a green and practical synthetic avenue to access spiro[5.5]trienone scaffolds, and the resulting products exhibit diverse synthetic versatility for subsequent structural modifications.

The Journal of Organic Chemistry
China Three Gorges Corporation (China) (CN), China Three Gorges University (CN)
Responsible consumption and production
Openalex Percentile: Top 20%
Radical Photochemical Reactions
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