Aryne Alder-Ene Reaction Enables Arylation of Conformationally Locked Styrenes

We report a transition metal-free aryne Alder-ene (AAE) reaction of conformationally locked styrenes like methylene indane (5,6-fusion) and methylene tetralin (6,6-fusion) to provide aryl-decorated indenes and dihydronaphthalenes. DFT studies compared the transition states between 5,6- and 6,6-fused systems. The synthetic utility of the 5,6- and 6,6-fused products was demonstrated.

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Publication Details

Journal
Organic Letters
Published
2025-04-15
DOI
https://doi.org/10.1021/acs.orglett.5c00511
Citations
3
Primary Topic
Cyclization and Aryne Chemistry
Type
article
Field-Weighted Citation Impact
2.81

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article

Aryne Alder-Ene Reaction Enables Arylation of Conformationally Locked Styrenes

Tamal Ballav, S. C. Barman, Venkataraman Ganesh
3 citations
Organic Letters
Cyclization and Aryne Chemistry
2.81
article

Aryne Alder-Ene Reaction Enables Arylation of Conformationally Locked Styrenes

Tamal Ballav, S. C. Barman, Venkataraman Ganesh
article en
3 citations

Abstract

We report a transition metal-free aryne Alder-ene (AAE) reaction of conformationally locked styrenes like methylene indane (5,6-fusion) and methylene tetralin (6,6-fusion) to provide aryl-decorated indenes and dihydronaphthalenes. DFT studies compared the transition states between 5,6- and 6,6-fused systems. The synthetic utility of the 5,6- and 6,6-fused products was demonstrated.

Organic LettersVol. 27(16)
Indian Institute of Technology Kharagpur (IN)
Council of Scientific and Industrial Research, India, Science and Engineering Research Board
Openalex Percentile: Top 11%
Cyclization and Aryne Chemistry
2.81
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