Citation: Zhang Ping, Shi Haonan, Zhang Tianshu, Cai Peijun, Jiang Bo, Tu Shujiang. Alkynylphosphonation of Unactivated Olefins via Radical-Triggered 1, 2-Alkynyl Migration[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 423-431. doi: 10.6023/cjoc201909007 shu

Alkynylphosphonation of Unactivated Olefins via Radical-Triggered 1, 2-Alkynyl Migration

Zhang Ping ^a,c ,
Shi Haonan ^b ,
Zhang Tianshu ^a ,
Cai Peijun ^a,, ,
Jiang Bo ^b ,
Tu Shujiang ^b,,

a.
School of Chemical Engineering & Technology, China University of Mining and Technology, Xuzhou, Jiangsu 221116
b.
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
c.
Jiangsu Provincial Xuzhou Pharmaceutical Vocational College, Xuzhou, Jiangsu 221116

Corresponding author: Cai Peijun, pjcai@cumt.edu.cn Tu Shujiang, laotu@jsnu.edu.cn
Received Date: 4 September 2019
Revised Date: 16 October 2019
Available Online: 25 February 2019
Fund Project: the Fundamental Research Funds for the Central Universities JH180263Project supported by the Fundamental Research Funds for the Central Universities (No. JH180263)

Figures(3)

A silver-mediated alkynylphosphonation of 1, 4-enynes with diarylphosphine oxides has been developed, by which a wide range of γ-ketophosphine oxides with moderate to good yields were synthesized through radical 1, 2-alkynyl migration. The transformation proceeded with sequential P-centered radical addition to vinyl unit, 3-exo-dig cyclization and 1, 2-alkynyl migration, resulting in the bond-forming events including C-P and C-C bonds to realize difunctionalization of unactivated olefins.
- 1, 4-enynes,
- alkynylphosphonation,
- γ-ketophosphine oxides,
- alkynyl migration,
- radical chemistry
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