Intermolecular oxidative Friedel-Crafts reaction triggered ring expansion affording 9,10-diarylphenanthrenes

Tienan Jin; Lu Yang; Ilya Gridnev; Masahiro Terada

doi:10.1021/acs.orglett.0c03283

Intermolecular oxidative Friedel-Crafts reaction triggered ring expansion affording 9,10-diarylphenanthrenes

Tienan Jin, Lu Yang, Ilya Gridnev, Masahiro Terada

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

5 Citations (Scopus)

Abstract

A novel intermolecular tandem oxidative aromatic coupling between arylidene fluorenes and unfunctionalized aromatics mediated by a DDQ/TFA oxidation system has been developed for the construction of 9,10-diary-lphenanthrenes (DAPs). The formation of a benzylic carbocation species possessing a quaternary sp³-carbon center on the fluorene moiety by an intermolecular oxidative Friedel-Crafts reaction of two different arenes successfully triggered the subsequent ring expansion to afford DAPs.

Original language	English
Pages (from-to)	8920-8924
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.0c03283
Publication status	Published - 2020 Nov 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c03283

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title = "Intermolecular oxidative Friedel-Crafts reaction triggered ring expansion affording 9,10-diarylphenanthrenes",

abstract = "A novel intermolecular tandem oxidative aromatic coupling between arylidene fluorenes and unfunctionalized aromatics mediated by a DDQ/TFA oxidation system has been developed for the construction of 9,10-diary-lphenanthrenes (DAPs). The formation of a benzylic carbocation species possessing a quaternary sp3-carbon center on the fluorene moiety by an intermolecular oxidative Friedel-Crafts reaction of two different arenes successfully triggered the subsequent ring expansion to afford DAPs.",

author = "Tienan Jin and Lu Yang and Ilya Gridnev and Masahiro Terada",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant No. JP16H00996 in Precisely Designed Catalysts with Customized Scaffolding and a Grant-in-Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand” (No. JP17H06447) from MEXT (Japan). Publisher Copyright: {\textcopyright} 2020 American Chemical Society. All rights reserved.",

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AU - Jin, Tienan

AU - Yang, Lu

AU - Gridnev, Ilya

AU - Terada, Masahiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant No. JP16H00996 in Precisely Designed Catalysts with Customized Scaffolding and a Grant-in-Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand” (No. JP17H06447) from MEXT (Japan). Publisher Copyright: © 2020 American Chemical Society. All rights reserved.

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N2 - A novel intermolecular tandem oxidative aromatic coupling between arylidene fluorenes and unfunctionalized aromatics mediated by a DDQ/TFA oxidation system has been developed for the construction of 9,10-diary-lphenanthrenes (DAPs). The formation of a benzylic carbocation species possessing a quaternary sp3-carbon center on the fluorene moiety by an intermolecular oxidative Friedel-Crafts reaction of two different arenes successfully triggered the subsequent ring expansion to afford DAPs.

AB - A novel intermolecular tandem oxidative aromatic coupling between arylidene fluorenes and unfunctionalized aromatics mediated by a DDQ/TFA oxidation system has been developed for the construction of 9,10-diary-lphenanthrenes (DAPs). The formation of a benzylic carbocation species possessing a quaternary sp3-carbon center on the fluorene moiety by an intermolecular oxidative Friedel-Crafts reaction of two different arenes successfully triggered the subsequent ring expansion to afford DAPs.

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Intermolecular oxidative Friedel-Crafts reaction triggered ring expansion affording 9,10-diarylphenanthrenes

Abstract

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