异构化
磷化氢
化学
催化作用
烯烃纤维
烯烃
氧化膦
镍
环氧化物
光化学
组合化学
有机化学
作者
Lin Huang,En Qi Lim,Ming Joo Koh
出处
期刊:Chem catalysis
[Elsevier]
日期:2022-03-01
卷期号:2 (3): 508-518
被引量:16
标识
DOI:10.1016/j.checat.2021.12.014
摘要
Catalytic systems that are readily modifiable to achieve olefin migration or remote functionalization are highly sought after in chemical synthesis. Here, we show that the combination of a commercially available nickel(II) pre-catalyst and a secondary phosphine oxide ligand enables site- and stereoselective alkene transposition for up to nine double-bond migrations within terminal and internal olefins under mild reductive conditions. Substrates bearing diverse functionalities including Brønsted acidic and reducible carbonyl groups are tolerated. Mechanistic and spectroscopic studies revealed the in situ generation of a catalytically active nickel-hydride species triggered by oxidative addition of the phosphine oxide. The reaction is amenable to regioconvergent isomerization as well as β-selective remote hydrophosphination when stoichiometric secondary phosphine oxide and base were employed.
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