Synthesis of Symmetrical 1, 3-Diynes via Cross-Coupling Reaction of Alkynyl Bromide with Alkynyl Aluminum Catalyzed by Nickel

doi:10.6023/cjoc201802019

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1538-1543.DOI: 10.6023/cjoc201802019 Previous Articles Next Articles

Notes

金属镍催化炔基铝与炔溴高效合成对称1,3-二炔化合物

张刚, 杓学蓓, 李清寒, 杨学军

西南民族大学化学与环境保护工程学院成都 610041

收稿日期:2018-02-14 修回日期:2018-04-04 发布日期:2018-05-17
通讯作者: 李清寒,E-mail:lqhchem@163.com E-mail:lqhchem@163.com
基金资助:
西南民族大学研究生创新基金（No.CX2016SZ063）和四川省科厅科技支撑（No.2015NZ0033）资助项目.

Synthesis of Symmetrical 1, 3-Diynes via Cross-Coupling Reaction of Alkynyl Bromide with Alkynyl Aluminum Catalyzed by Nickel

Zhang Gang, Shao Xuebei, Li Qinghan, Yang Xuejun

College of Chemistry and Environmental Protection Engineering, Southwest Minzu University, Chengdu 610041

Received:2018-02-14 Revised:2018-04-04 Published:2018-05-17
Contact: 10.6023/cjoc201802019 E-mail:lqhchem@163.com
Supported by:
Project supported by the Postgraduate Degree Construction Project of Southwest University for Nationalities (No. CX2016SZ063) and the Sichuan Provincial Department of Science and Technology Support Program (No. 2015NZ0033).

1. Synthesis of Symmetrical 1, 3-Diynes via Cross-Coupling Reaction of Alkynyl Bromide with Alkynyl Aluminum Catalyzed by Nickel.PDF(2666KB)

Abstract

1,3-Diyne compounds are important inter mediates in organic synthesis, which are widely used in pharmaceutical chemistry, organic synthesis and materials science. A highly efficient for the synthesis of 1,3-diyne via cross-coupling of alkynyl bromides with alkynyl aluminium reagents catalyzed by nickel has been developed. The coupling reaction of alkynyl bromides with alkynyl aluminium reagents mediated by Ni(acac)₂ (5 mol%)/1,2-bis(diphenylphosphino)ethane nickel(Ⅱ) chloride (DPPE) (10 mol%)in 1,2-dimethoxyethane afforded the corresponding coupling products 1,3-diyne in good to excellent yields(up to 90%) at room temperature for 5 h. The coupling reaction of alkynyl aluminum with different substituents and alkynyl bromine with various substituents can afforded the coupling products in good yields. Importantly, the α-ethynylnaphthalene and 2-ethynylthiophene were also suitable for the reaction. This process is simple and easily performed, which provides an efficient method for the synthesis of 1,3-diynes derivatives.

Key words: 1,3-diyne, nickel, alkynyl bromide, alkynyl aluminium, cross-coupling

Cite this article

Zhang Gang, Shao Xuebei, Li Qinghan, Yang Xuejun. Synthesis of Symmetrical 1, 3-Diynes via Cross-Coupling Reaction of Alkynyl Bromide with Alkynyl Aluminum Catalyzed by Nickel[J]. Chin. J. Org. Chem., 2018, 38(6): 1538-1543.

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金属镍催化炔基铝与炔溴高效合成对称1,3-二炔化合物

Synthesis of Symmetrical 1, 3-Diynes via Cross-Coupling Reaction of Alkynyl Bromide with Alkynyl Aluminum Catalyzed by Nickel

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