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Photochemical, Nickel-Catalyzed C(sp3)–C(sp3) Reductive Cross-Coupling of α-Silylated Alkyl Electrophiles and Allylic Sulfones
ACS Catalysis ( IF 12.9 ) Pub Date : 2022-08-11 , DOI: 10.1021/acscatal.2c03070
Yan Xu 1 , Muliang Zhang 1 , Martin Oestreich 1
Affiliation  

A nickel-catalyzed C(sp3)–C(sp3) cross-electrophile coupling between α-silylated alkyl bromides and an allylic sulfone is reported. Instead of a metal as the stoichiometric reductant, this photochemical reductive process relies on a Hantzsch ester but does not require an exogenous photocatalyst. The role of the silyl group in the α-position and its stabilizing effect on the assumed carbon-centered radical intermediate is demonstrated. The functional-group tolerance is excellent, allowing for the synthesis of various homoallylic silanes.

中文翻译:

α-甲硅烷基化烷基亲电子试剂和烯丙基砜的光化学、镍催化 C(sp3)–C(sp3) 还原交叉偶联

报道了 α-甲硅烷基化烷基溴和烯丙基砜之间的镍催化 C(sp 3 )–C(sp 3 ) 交叉亲电偶联。代替金属作为化学计量还原剂,这种光化学还原过程依赖于 Hantzsch 酯,但不需要外源光催化剂。证明了甲硅烷基在 α 位的作用及其对假定的碳中心自由基中间体的稳定作用。官能团耐受性极佳,可用于合成各种均烯丙基硅烷。
更新日期:2022-08-11
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