Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.
Key Laboratory of Molecular Target & Clinical Pharmacology, State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, China.
Nat Commun. 2020 Oct 7;11(1):5036. doi: 10.1038/s41467-020-18834-6.
Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky's N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.
烷基羧酸和伯胺在生物科学、药物科学、化学科学和材料科学的各个方面都无处不在。通过分别化学转化为氧化还原活性酯（RAE）和 Katritzky 的 N-烷基吡啶鎓盐，烷基羧酸和伯胺可用作构建新连接的理想起始材料。在这项工作中，揭示了 Mn 介导的活化脂肪族酸和伯胺的还原性脱羧/脱氨官能化。在简单温和的反应条件下，高效构建了一系列 C-X（X=S、Se、Te、H、P）和 C-C 键。该方案适用于一些结构复杂的天然产物或药物的后期修饰。初步的机理研究表明，反应途径中涉及自由基。
