A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation

Sachin S. Ichake; Bharath Kumar Villuri; Sabbasani Rajasekhara Reddy; Veerababurao Kavala; Ching Fa Yao

doi:10.1021/acs.orglett.9b00532

A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation

Sachin S. Ichake, Bharath Kumar Villuri, Sabbasani Rajasekhara Reddy, Veerababurao Kavala, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

9 Citations (Scopus)

Abstract

The palladium catalyzed synthesis of 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives as core polycyclic aromatic hydrocarbons (PAHs) was achieved via an intramolecular annulation and decyanogenative C-H bond alkenylation strategy. A readily synthesized Knoevenagel condensation product of [1,1′-biphenyl]-2,2′-dicarbaldehyde with benzyl cyanide converted successfully into 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives in excellent yields up to 94%. The transformation involves an intramolecular cascade C-C bond formation along with a C-H bond cleavage sequence.

Original language	English
Pages (from-to)	2256-2260
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.9b00532
Publication status	Published - 2019 Apr 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b00532

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A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation. / Ichake, Sachin S.; Villuri, Bharath Kumar; Reddy, Sabbasani Rajasekhara et al.
In: Organic Letters, Vol. 21, No. 7, 05.04.2019, p. 2256-2260.

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

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title = "A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation",

abstract = "The palladium catalyzed synthesis of 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives as core polycyclic aromatic hydrocarbons (PAHs) was achieved via an intramolecular annulation and decyanogenative C-H bond alkenylation strategy. A readily synthesized Knoevenagel condensation product of [1,1′-biphenyl]-2,2′-dicarbaldehyde with benzyl cyanide converted successfully into 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives in excellent yields up to 94%. The transformation involves an intramolecular cascade C-C bond formation along with a C-H bond cleavage sequence.",

author = "Ichake, {Sachin S.} and Villuri, {Bharath Kumar} and Reddy, {Sabbasani Rajasekhara} and Veerababurao Kavala and Yao, {Ching Fa}",

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AU - Reddy, Sabbasani Rajasekhara

AU - Kavala, Veerababurao

AU - Yao, Ching Fa

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N2 - The palladium catalyzed synthesis of 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives as core polycyclic aromatic hydrocarbons (PAHs) was achieved via an intramolecular annulation and decyanogenative C-H bond alkenylation strategy. A readily synthesized Knoevenagel condensation product of [1,1′-biphenyl]-2,2′-dicarbaldehyde with benzyl cyanide converted successfully into 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives in excellent yields up to 94%. The transformation involves an intramolecular cascade C-C bond formation along with a C-H bond cleavage sequence.

AB - The palladium catalyzed synthesis of 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives as core polycyclic aromatic hydrocarbons (PAHs) was achieved via an intramolecular annulation and decyanogenative C-H bond alkenylation strategy. A readily synthesized Knoevenagel condensation product of [1,1′-biphenyl]-2,2′-dicarbaldehyde with benzyl cyanide converted successfully into 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives in excellent yields up to 94%. The transformation involves an intramolecular cascade C-C bond formation along with a C-H bond cleavage sequence.

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A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation

Abstract

ASJC Scopus subject areas

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CCDC 1895399: Experimental Crystal Structure Determination

CCDC 1895434: Experimental Crystal Structure Determination

CCDC 1837256: Experimental Crystal Structure Determination

Cite this

A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1895399: Experimental Crystal Structure Determination

CCDC 1895434: Experimental Crystal Structure Determination

CCDC 1837256: Experimental Crystal Structure Determination

Cite this