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一种通过钯催化分子内环化/脱氰基C-H键烯基化构建功能化三亚苯骨架的合成策略。

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

作者信息

Ichake Sachin S, Villuri Bharath Kumar, Reddy Sabbasani Rajasekhara, Kavala Veerababurao, Yao Ching-Fa

机构信息

Department of Chemistry , National Taiwan Normal University , 88, Sec. 4, Ting-Chow Road , Taipei - 116 , Taiwan R.O.C.

Department of Chemistry, School of Advanced Sciences , Vellore Institute of Technology (VIT) , Vellore 632014 , India.

出版信息

Org Lett. 2019 Apr 5;21(7):2256-2260. doi: 10.1021/acs.orglett.9b00532. Epub 2019 Mar 18.

DOI:10.1021/acs.orglett.9b00532
PMID:30883138
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.

摘要

通过分子内环化和脱氰基C-H键烯基化策略实现了钯催化合成作为核心多环芳烃(PAHs)的14-苯基苯并[f]四苯并-9-甲腈衍生物。[1,1'-联苯]-2,2'-二甲醛与苄基氰的易于合成的克诺文纳格尔缩合产物成功地以高达94%的优异产率转化为14-苯基苯并[f]四苯并-9-甲腈衍生物。该转化涉及分子内级联C-C键形成以及C-H键裂解序列。

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