4.8 Article

Z-Selective Addition of Diaryl Phosphine Oxides to Alkynes via Photoredox Catalysis

期刊

ACS CATALYSIS
卷 8, 期 11, 页码 10599-10605

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b02617

关键词

Z-selectivity; pi-pi stacking interaction; terminal and internal alkynes; gram-scale synthesis; radical addition

资金

  1. National Natural Science Foundation of China [21390402, 21520102003]
  2. Hubei Province Natural Science Foundation of China [2017CFA010, 2016CFB571]

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Radical addition to alkynes is known to predominantly yield thermodynamically more stable E-alkenes. Control of stereoselectivity in these reactions, and the isolation of the higher-energy Z-alkenes, remain an important challenge in chemical synthesis. Herein, direct synthesis of Z-alkenylphosphine oxides via visible-light-induced radical addition to alkynes in water is reported. This protocol was effective with various terminal and internal alkynes, affording products with high Z-stereoselectivity. Moreover, this transformation was demonstrated on gram scale. Mechanistic studies support the following conclusions: (1) the reaction proceeds via free-radical addition; (2) the choice of K2CO3 as aqueous base is crucial to the transformation; and (3) pi-pi stacking interaction greatly improves Z-selectivity.

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