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Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts
Synlett ( IF 1.7 ) Pub Date : 2020-06-16 , DOI: 10.1055/s-0040-1707817 Hideki Yorimitsu , Hiroko Minami , Keisuke Nogi
Synlett ( IF 1.7 ) Pub Date : 2020-06-16 , DOI: 10.1055/s-0040-1707817 Hideki Yorimitsu , Hiroko Minami , Keisuke Nogi
Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C–S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S-methylation with MeOTf. Mechanistic experiments suggest that C–S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C–S cleavage and radical recombination step.
中文翻译:
三烷基锍盐的镍催化根岸型芳基化
三烷基锍盐与芳基锌试剂的 Negishi 型芳基化反应已在镍催化下完成。发现使用环己硫醇作为额外的配体对于促进 C-S 裂解特别重要。本反应通过与 MeOTf 的 S-甲基化相结合,实现了二烷基硫醚的一锅芳基化。机理实验表明,C-S 裂解将通过单电子转移 (SET) 进行以产生最稳定的以碳为中心的自由基,并且硫醇盐配体将促进 C-S 裂解和自由基重组步骤。
更新日期:2020-06-16
中文翻译:
三烷基锍盐的镍催化根岸型芳基化
三烷基锍盐与芳基锌试剂的 Negishi 型芳基化反应已在镍催化下完成。发现使用环己硫醇作为额外的配体对于促进 C-S 裂解特别重要。本反应通过与 MeOTf 的 S-甲基化相结合,实现了二烷基硫醚的一锅芳基化。机理实验表明,C-S 裂解将通过单电子转移 (SET) 进行以产生最稳定的以碳为中心的自由基,并且硫醇盐配体将促进 C-S 裂解和自由基重组步骤。