Assembly of 5H-dibenzo[a,d]cycloheptenes by a formal [5 + 2] annulation of ortho-aryl alkynyl benzyl alcohols with arenes

Zhebing Zhang; Tao Cai; Zhaohui Zhan; Huiting Xu; Lemao Yu; Xiang Luo; Chunmei Li; Yuzhen Gao; Xuemei Wei; Xinzhi Chen; Runpu Shen

doi:10.1039/D2OB01335E

Assembly of 5H-dibenzo[a,d]cycloheptenes by a formal [5 + 2] annulation of ortho-aryl alkynyl benzyl alcohols with arenes†

Zhebing Zhang,^a Tao Cai,

*^abc Zhaohui Zhan,^a Huiting Xu,^a Lemao Yu,

^a Xiang Luo,^a Chunmei Li,^a Yuzhen Gao,

^d Xuemei Wei,^a Xinzhi Chen*^c and Runpu Shen*^ab

Author affiliations

* Corresponding authors

^a College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, China
E-mail: cait361@usx.edu.cn

^b Zhejiang Engineering Research Center of Fat-Soluble Vitamin, China
E-mail: srunpu@usx.edu.cn

^c College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, China
E-mail: xzchen@zju.edu.cn

^d Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China

Abstract

A new synthetic methodology for the synthesis of 5H-dibenzo[a,d]cycloheptenes from ortho-aryl alkynyl benzyl alcohols and arenes via a Tf₂O-mediated formal [5 + 2] annulation reaction has been achieved. From this transformation, structurally diverse 5H-dibenzo[a,d]cycloheptenes were achieved in moderate to good yields. This transformation probably involves an intermolecular Friedel–Crafts-type alkylation and a subsequent intramolecular 7-endo-dig cyclization in one pot, highlighting the high efficiency, regioselectivity, and step-economy of this protocol.

Organic & Biomolecular Chemistry

Assembly of 5H-dibenzo[a,d]cycloheptenes by a formal [5 + 2] annulation of ortho-aryl alkynyl benzyl alcohols with arenes†

Abstract

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Assembly of 5H-dibenzo[a,d]cycloheptenes by a formal [5 + 2] annulation of ortho-aryl alkynyl benzyl alcohols with arenes

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