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Photoinduced C(sp3)–H Chalcogenation of Amide Derivatives and Ethers via Ligand-to-Metal Charge-Transfer
Organic Letters ( IF 5.2 ) Pub Date : 2022-06-21 , DOI: 10.1021/acs.orglett.2c01505
Ben Niu 1 , Krishnakumar Sachidanandan 1 , Maria Victoria Cooke 1 , Taylor E Casey 1 , Sébastien Laulhé 1
Affiliation  

A photoinduced, iron(III) chloride-catalyzed C–H activation of N-methyl amides and ethers leads to the formation of C–S and C–Se bonds via a ligand-to-metal charge transfer (LMCT) process. This methodology converts secondary and tertiary amides, sulfonamides, and carbamates into the corresponding amido-N,S-acetal derivatives in good yields. Mechanistic work revealed that this transformation proceeds through a hydrogen atom transfer (HAT) involving chlorine radical intermediates.

中文翻译:

通过配体到金属的电荷转移对酰胺衍生物和醚进行光诱导 C(sp3)–H 硫属化

光诱导的氯化铁 (III) 催化的N-甲基酰胺和醚的 C-H 活化导致通过配体到金属电荷转移 (LMCT) 过程形成 C-S 和 C-Se 键。该方法将仲和叔酰胺、磺酰胺和氨基甲酸酯以良好的收率转化为相应的酰胺-N,S-缩醛衍生物。机理研究表明,这种转变是通过涉及氯自由基中间体的氢原子转移 (HAT) 进行的。
更新日期:2022-06-21
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