A copper-catalyzed three-component reaction of alkenes, cycloketone oximes and DABCO·(SO2)2: Direct C(sp2)-H cyanoalkylsulfonylation,Chinese Chemical Letters

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A copper-catalyzed three-component reaction of alkenes, cycloketone oximes and DABCO·(SO2)2: Direct C(sp2)-H cyanoalkylsulfonylation
Chinese Chemical Letters ( IF 9.4 ) Pub Date : 2021-11-10 , DOI: 10.1016/j.cclet.2021.11.009
Yating Liu ₁ , Luoyu Wang ₁ , Ling-Hui Zeng ₂ , Yun Zhao ₁ , Tonghao Zhu ₁ , Jie Wu _{1,

3,

4}

Affiliation

A copper-catalyzed three-component reaction of alkenes, cycloketone oximes and DABCO·(SO₂)₂ is developed, which provides a convenient route for the synthesis of diverse (E)-cyanoalkylsulfonyl alkenes in moderate to good yields with excellent regio- and stereoselectivity. A broad substrate scope with excellent functional group tolerance is observed. A plausible radical pathway is proposed, which involves copper-catalyzed ring-opening C single bond C bond cleavage of O-acyl oxime and insertion of sulfur dioxide. During the reaction process, cyanoalkyl radical and cyanoalkylsulfonyl radical are the key intermediates.

中文翻译：

铜催化烯烃、环酮肟和 DABCO·(SO2)2 的三组分反应：直接 C(sp2)-H 氰基烷基磺酰化

开发了一种铜催化烯烃、环酮肟和 DABCO·(SO ₂ ) ₂的三组分反应，为以中等至高产率合成多种 ( E )-氰基烷基磺酰基烯烃提供了一条便捷的途径，具有优异的区域和立体选择性。观察到具有优异官能团耐受性的广泛底物范围。提出了一种似是而非的自由基途径，其涉及铜催化的O-酰基肟的开环 C C 键断裂和二氧化硫的插入。在反应过程中，氰基烷基自由基和氰基烷基磺酰基自由基是关键的中间体。

更新日期：2021-11-10

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