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通过铁催化的自由基接力实现C(sp)-H键的远程叠氮化以合成δ-叠氮基磺酰胺

Remote azidation of C(sp)-H bonds to synthesize δ-azido sulfonamides via iron-catalyzed radical relay.

作者信息

Bian Kang-Jie, Wang Cheng-Yu, Huang Yu-Ling, Xu Yi-Hao, Wang Xi-Sheng

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, Center for Excellence in Molecular Synthesis of CAS, University of Science and Technology of China, Hefei, Anhui 230026, China.

出版信息

Org Biomol Chem. 2020 Jul 22;18(28):5354-5358. doi: 10.1039/d0ob00964d.

DOI:10.1039/d0ob00964d
PMID:32643742
Abstract

With an iron catalyst playing dual roles as a radical initiator and terminator, we report a selective remote C-H functionalization to access δ-azido sulfonamides through a radical relay process. The reaction of N-fluorosulfonamide furnishes the corresponding products in excellent yields with high regioselective control. The key to success is the highly efficient iron-mediated redox azido transfer to the in situ generated carbon radical. The products provide incentives for drug discovery and ligand designs.

摘要

通过铁催化剂同时作为自由基引发剂和终止剂的双重作用,我们报道了一种选择性远程C-H官能化反应,可通过自由基接力过程合成δ-叠氮基磺酰胺。N-氟磺酰胺的反应以优异的产率和高区域选择性控制提供了相应的产物。成功的关键是铁介导的氧化还原叠氮基高效转移到原位生成的碳自由基上。这些产物为药物发现和配体设计提供了动力。

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