A Mechanism Study for Self-Cleaving Chlorotetrafluoroethylsulfinyl (−SOCF2CF2Cl)-Directed Pd(II)-Catalyzed C–H Activation,The Journal of Organic Chemistry

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A Mechanism Study for Self-Cleaving Chlorotetrafluoroethylsulfinyl (−SOCF2CF2Cl)-Directed Pd(II)-Catalyzed C–H Activation
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-11-16 , DOI: 10.1021/acs.joc.1c01852
Nan-Qi Shao ₁ , Dong-Hui Wang _{1,

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Affiliation

A mechanism study for Pd(II)-catalyzed C(sp³)–H activation using a self-cleaving chlorotetrafluoroethylsulfinyl (−SOCF₂CF₂Cl) auxiliary as a directing group is reported. Mechanistic studies reveal that (1) the auxiliary group is crucial for C(sp³)–H activation, (2) the reaction undergoes a C(sp³)–H olefination–Michael addition–removal of the auxiliary sequence, (3) the removal of the auxiliary (SOR_f) is most likely the alcoholic solvolysis of the −SOCF₂CF₂Cl group on the N-tri-substituted sulfonamides, and (4) the C(sp³)–H cleavage is involved in the rate-determining step.

中文翻译：

自裂解氯四氟乙基亚磺酰基 (-SOCF2CF2Cl) 定向 Pd(II) 催化 C-H 活化的机理研究

报道了使用自裂解氯四氟乙基亚磺酰基 (-SOCF ₂ CF ₂ Cl) 助剂作为导向基团的 Pd(II) 催化 C(sp ^{3 )-H 活化的机理研究。}机理研究表明（1）辅助基团对 C(sp ³ )-H 活化至关重要，(2) 反应经历了 C(sp ³ )-H 烯化-迈克尔加成-辅助序列的去除，(3)助剂 (SOR _f ) 的去除很可能是N-三取代磺酰胺上的 -SOCF ₂ CF ₂ Cl 基团的醇溶剂解，并且 (4) C(sp ³ )-H 裂解参与了速率确定步骤。

更新日期：2021-12-03

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