Discovery of an Oxidative System for Radical Generation from Csp3–H Bonds: A Synthesis of Functionalized Oxindoles

Autor:	Yan-Hao Liu, Ming-Zhong Zhang, Jin-Xing Yin, Chong Li, Wan-Ting Li, Tieqiao Chen, Huisheng Huang, Xin Yang, Qi Wang, Yuan-Yuan Li
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Radical Organic Chemistry Functional group Polycarbonyl Salt (chemistry) Alkylbenzenes Oxidative phosphorylation Persulfate Combinatorial chemistry
Zdroj:	The Journal of Organic Chemistry. 86:15544-15557
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c02032
Popis:	A facile and versatile method for generating radicals from Csp3-H bonds under metal-free and organic-peroxide-free conditions was developed. By combining safe persulfate and low-toxic quaternary ammonium salt, a wide variety of Csp3-H compounds including ethers, (hetero)aromatic/aliphatic ketones, alkylbenzenes, alkylheterocycles, cycloalkanes, and haloalkanes were selectively activated to generate the corresponding C-centered radicals, which could be further captured by N-arylacrylamides to deliver the valuable functionalized oxindoles. Good functional group tolerance was demonstrated. The useful polycarbonyl compound and esters were also modified with the strategy. Moreover, the combination can also be applied to the practical coupling between simple haloalkanes and N-hydroxyphthalimide (NHPI).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3522de3535be5b4131c01301ae013a06 https://doi.org/10.1021/acs.joc.1c02032 Zobrazit plný text záznamu