Cyclization/hydrolysis of 1,5-enenitriles initiated by sulfonyl radicals in the aqueous phase in the presence of the I2/TBHP system

• Published in: Organic & biomolecular chemistry Vol. 20; no. 32; pp. 6418 - 6422
• Main Authors: Hu, Sen-Jie, Jiang, Li-Lin, Qiu, Hui, Luo, Chun-Mei, Guan, Yu-Tao, Li, Long, Dong, Youren, Lei, Ke-Wei, Wei, Wen-Ting
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 17.08.2022; Royal Society of Chemistry
• Subjects: Butyl hydroperoxide; Catalysts; Chemistry; Chemistry, Organic; Hydrazides; Hydrolysis; Oxidants; Oxidation; Oxidizing agents; Physical Sciences; Pyrrolidine; Radicals; Science & Technology; ORGANIC-SYNTHESIS; TBHP; 1,6-ENYNES; HYDRAZIDES; ADDITION/CYCLIZATION CASCADE; CHEMISTRY; SULFUR; ALKYNES; ACCESS; WATER
• ISSN: 1477-0520; 1477-0539; 1477-0539
• DOI: 10.1039/d2ob01124g

A novel cyclization/hydrolysis of 1,5-enenitriles for the synthesis of valuable pyrrolidine-2,4-diones in the aqueous phase using I-2 as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant is reported. In the presence of the I-2/TBHP system, sulfonyl hydrazides produce sulfonyl radicals,...