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

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,...

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Published inOrganic & 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
LanguageEnglish
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
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Summary: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, which undergo radical addition, intramolecular cyclization, hydrogen abstraction, and hydrolysis to give the final products. The use of the inexpensive and environmentally friendly I-2/TBHP catalytic oxidation system in the aqueous phase makes it a benign and sustainable strategy.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d2ob01124g