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

doi:10.6023/cjoc201909007

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 423-431.DOI: 10.6023/cjoc201909007 Previous Articles Next Articles

利用自由基引发的1,2-炔基迁移实现非活性烯烃的炔膦酰化

张萍^a,c, 石浩楠^b, 张天舒^a, 蔡佩君^a, 姜波^b, 屠树江^b

a 中国矿业大学化工学院江苏徐州 221116;
b 江苏师范大学化学与材料科学学院江苏徐州 221116;
c 江苏省徐州医药高等职业学校江苏徐州 221116

收稿日期:2019-09-04 修回日期:2019-10-16 发布日期:2019-10-25
通讯作者: 蔡佩君, 屠树江 E-mail:pjcai@cumt.edu.cn;laotu@jsnu.edu.cn
基金资助:
中央高校基本科研专项资金基金（No.JH180263）资助项目.

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

Received:2019-09-04 Revised:2019-10-16 Published:2019-10-25
Supported by:
Project supported by the Fundamental Research Funds for the Central Universities (No. JH180263).

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Abstract

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.

Key words: 1,4-enynes, alkynylphosphonation, γ-ketophosphine oxides, alkynyl migration, radical chemistry

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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.

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利用自由基引发的1,2-炔基迁移实现非活性烯烃的炔膦酰化

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

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