Intermolecular alkene arylcyanation using BnSCN as a cyanide source via a reductive strategy: access to 3,3-disubstituted oxindoles,Organic Chemistry Frontiers

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Intermolecular alkene arylcyanation using BnSCN as a cyanide source via a reductive strategy: access to 3,3-disubstituted oxindoles
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-1-6 , DOI: 10.1039/d0qo01462a
Yunxia Feng _{1,

2,

3,

4} , Shen Zhao _{1,

2,

3,

4} , Guopeng Du _{1,

2,

3,

4} , Shuang Zhang _{1,

2,

3,

4} , Daopeng Zhang _{1,

2,

3,

4} , Hui Liu _{1,

2,

3,

4} , Xinjin Li _{1,

2,

3,

4} , Yunhui Dong _{1,

2,

3,

4} , Feng-Gang Sun _{1,

2,

3,

4}

Affiliation

Herein, a nickel-catalyzed two-component reductive arylcyanation of aryl (pseudo)halide tethered alkenes using benzyl thiocyanate as the cyanide source via C–S bond activation is developed. Using this protocol, a wide scope of 3,3-disubstituted oxindoles bearing all-carbon quaternary stereocenters are accessible in moderate to excellent yields. The preliminary mechanistic investigations reveal that a Ni(I)/Ni(III) process might be involved in the mechanism.

中文翻译：

通过还原策略使用BnSCN作为氰化物源的分子间烯烃芳基氰化反应：获得3,3-二取代的吲哚

在此，开发了使用镍硫氰酸酯作为氰化物源通过C–S键活化的镍催化的芳基（假）卤化物系链烯烃的二元还原性芳基氰化反应。使用该协议，可以以中等到极好的收率获得范围广泛的带有全碳四元立体中心的3,3-二取代的羟吲哚。初步的机理研究表明，该机理可能涉及Ni（I）/ Ni（III）过程。

更新日期：2021-01-14

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