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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

5 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	2256-2260
頁數	5
期刊	Organic Letters
卷	21
發行號	7
DOIs	https://doi.org/10.1021/acs.orglett.9b00532
出版狀態	已發佈 - 2019 4月 5

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

存取文件

10.1021/acs.orglett.9b00532

其它文件與鏈接

CCDC 1837015: Experimental Crystal Structure Determination
Ichake, S. S. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Kavala, V. (Creator) & Yao, C. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1znkkr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1znkkr&sid=DataCite
資料集: Dataset
CCDC 1895396: Experimental Crystal Structure Determination
Ichake, S. S. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Kavala, V. (Creator) & Yao, C. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc21m9tt, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21m9tt&sid=DataCite
資料集: Dataset
CCDC 1895399: Experimental Crystal Structure Determination
Ichake, S. S. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Kavala, V. (Creator) & Yao, C. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc21m9xx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21m9xx&sid=DataCite
資料集: Dataset

引用此

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 等.

於: Organic Letters, 卷 21, 編號 7, 05.04.2019, p. 2256-2260.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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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}",

note = "Funding Information: We are grateful to the Ministry of Science and Technology ROC (MOST 107-2113-M-003-003) and National Taiwan Normal University (103-07-C) for providing financial assistance. We are also thanking the Instrumentation Centre at National Taiwan Normal University. We are grateful to Xray technician Mr. Ting-Shen Kuo, Mass spectroscopy technician Ms. Hsiu-Min Huan, NMR technician Ms. Chiu- Hui He and Dr. Ram Ambre (UV Fluorescence studies) for providing the analytical data presented in this paper. Funding Information: We are grateful to the Ministry of Science and Technology ROC (MOST 107-2113-M-003-003) and National Taiwan Normal University (103-07-C) for providing financial assistance. We are also thanking the Instrumentation Centre at National Taiwan Normal University. We are grateful to X-ray technician Mr. Ting-Shen Kuo, Mass spectroscopy technician Ms. Hsiu-Min Huan, NMR technician Ms. Chiu-Hui He and Dr. Ram Ambre (UV Fluorescence studies) for providing the analytical data presented in this paper. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Kavala, Veerababurao

AU - Yao, Ching Fa

N1 - Funding Information: We are grateful to the Ministry of Science and Technology ROC (MOST 107-2113-M-003-003) and National Taiwan Normal University (103-07-C) for providing financial assistance. We are also thanking the Instrumentation Centre at National Taiwan Normal University. We are grateful to Xray technician Mr. Ting-Shen Kuo, Mass spectroscopy technician Ms. Hsiu-Min Huan, NMR technician Ms. Chiu- Hui He and Dr. Ram Ambre (UV Fluorescence studies) for providing the analytical data presented in this paper. Funding Information: We are grateful to the Ministry of Science and Technology ROC (MOST 107-2113-M-003-003) and National Taiwan Normal University (103-07-C) for providing financial assistance. We are also thanking the Instrumentation Centre at National Taiwan Normal University. We are grateful to X-ray technician Mr. Ting-Shen Kuo, Mass spectroscopy technician Ms. Hsiu-Min Huan, NMR technician Ms. Chiu-Hui He and Dr. Ram Ambre (UV Fluorescence studies) for providing the analytical data presented in this paper. Publisher Copyright: © 2019 American Chemical Society.

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1837015: Experimental Crystal Structure Determination

CCDC 1895396: Experimental Crystal Structure Determination

CCDC 1895399: Experimental Crystal Structure Determination

引用此