Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1538-1543. doi: 10.6023/cjoc201802019 shu

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

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

Corresponding author: Li Qinghan, lqhchem@163.com
Received Date: 14 February 2018
Revised Date: 4 April 2018
Available Online: 17 June 2018
Fund Project: the Sichuan Provincial Department of Science and Technology Support Program 2015NZ0033the Postgraduate Degree Construction Project of Southwest University for Nationalities CX2016SZ063Project 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).

Figures(1)

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.
- 1, 3-diyne,
- nickel,
- alkynyl bromide,
- alkynyl aluminium,
- cross-coupling
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