Radical Alkyne peri-Annulation Reactions for the Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene

Nikolay P. Tsvetkov; Edgar Gonzalez-Rodriguez; Audrey Hughes; Gabriel dos Passos Gomes; Frankie D. White; Febin Kuriakose; Igor V. Alabugin

doi:10.1002/anie.201712783

Radical Alkyne peri-Annulation Reactions for the Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene

Nikolay P. Tsvetkov, Edgar Gonzalez-Rodriguez, Audrey Hughes, Gabriel dos Passos Gomes, Frankie D. White, Febin Kuriakose, Igor V. Alabugin

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

Abstract

Radical cyclization reactions at a peri position were used for the synthesis of polyaromatic compounds. Depending on the choice of reaction conditions and substrate, this flexible approach led to Bu₃Sn-substituted phenalene, benzanthrene, and olympicene derivatives. Subsequent reactions with electrophiles provided synthetic access to previously inaccessible functionalized polyaromatic compounds.

Original language	English
Pages (from-to)	3651-3655
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	14
DOIs	https://doi.org/10.1002/anie.201712783
State	Published - Mar 26 2018
Externally published	Yes

Funding

We are grateful for the support of the National Science Foundation (Grant CHE-035678) and for the assistance of the FSU Research Computing Center.

Keywords

alkyne benzannulation
cyclization
polyaromatic compounds
radical reactions
zigzag edge

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10.1002/anie.201712783

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title = "Radical Alkyne peri-Annulation Reactions for the Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene",

abstract = "Radical cyclization reactions at a peri position were used for the synthesis of polyaromatic compounds. Depending on the choice of reaction conditions and substrate, this flexible approach led to Bu3Sn-substituted phenalene, benzanthrene, and olympicene derivatives. Subsequent reactions with electrophiles provided synthetic access to previously inaccessible functionalized polyaromatic compounds.",

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AU - Gonzalez-Rodriguez, Edgar

AU - Hughes, Audrey

AU - dos Passos Gomes, Gabriel

AU - White, Frankie D.

AU - Kuriakose, Febin

AU - Alabugin, Igor V.

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AB - Radical cyclization reactions at a peri position were used for the synthesis of polyaromatic compounds. Depending on the choice of reaction conditions and substrate, this flexible approach led to Bu3Sn-substituted phenalene, benzanthrene, and olympicene derivatives. Subsequent reactions with electrophiles provided synthetic access to previously inaccessible functionalized polyaromatic compounds.

KW - alkyne benzannulation

KW - cyclization

KW - polyaromatic compounds

KW - radical reactions

KW - zigzag edge

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Radical Alkyne peri-Annulation Reactions for the Synthesis of Functionalized Phenalenes, Benzanthrenes, and Olympicene

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