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由α-溴代环状N-磺酰亚胺生成α-亚胺基自由基及其在光氧化还原催化剂作用下与各种自由基受体偶联反应中的应用

Generation of α-Iminyl Radicals from α-Bromo Cyclic N-Sulfonylimines and Application to Coupling with Various Radical Acceptors Using a Photoredox Catalyst.

作者信息

Esumi Naoto, Suzuki Kensuke, Nishimoto Yoshihiro, Yasuda Makoto

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.

Frontier Research Base for Global Young Researchers Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, 565-0871, Japan.

出版信息

Chemistry. 2018 Jan 9;24(2):312-316. doi: 10.1002/chem.201704060. Epub 2017 Oct 26.

DOI:10.1002/chem.201704060
PMID:28977705
Abstract

Visible-light-induced generation of α-iminyl radicals was accomplished using α-bromo cyclic N-sulfonylimines and photoredox catalysts such as erythrosine B or Ru(bpy) (PF ) . The generated α-iminyl radical was utilized for various radical reactions with allylation reagents, silyl enol ethers and allenyl stannane to give the corresponding coupling products. Furthermore, atom transfer radical addition (ATRA) to olefin proceeded to provide the ATRA product. This process provided a mild and efficient method for the synthesis of cyclic N-sulfonylimine-containing molecules that act as bioactive compounds and become the precursors in sultam synthesis.

摘要

使用α-溴代环状N-磺酰亚胺和光氧化还原催化剂(如赤藓红B或Ru(bpy) (PF ) )实现了可见光诱导的α-亚胺基自由基的生成。所生成的α-亚胺基自由基被用于与烯丙基化试剂、硅烯醇醚和烯丙基锡烷进行各种自由基反应,以得到相应的偶联产物。此外,烯烃的原子转移自由基加成(ATRA)反应也能顺利进行,从而提供ATRA产物。该过程为合成含环状N-磺酰亚胺的分子提供了一种温和且高效的方法,这些分子可作为生物活性化合物,并成为氮杂环丁砜合成中的前体。

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