An efficient iodine pentoxide-triggered iodocarbocyclization for the synthesis of iodooxindoles in water

An efficient iodocarbocyclization of alkenes for the synthesis of iodooxindoles has been developed. This reaction proceeds in a chemoselective manner and shows excellent tolerance of various functional groups, including a chemosensitive hydroxymethyl group. Nonmetal inorganic iodine pentoxide was us...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 28; pp. 5197 - 5202
Main Authors Zhang, Ming-Zhong, Wang, Xin, Gong, Ming-Ying, Chen, Lin, Shi, Wen-Bing, He, Shu-Hua, Jiang, Yong, Chen, Tieqiao
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Alkenes
Chemical synthesis
Chemistry
Chemistry, Organic
Functional groups
Iodine
Physical Sciences
Reaction mechanisms
Science & Technology
METAL-FREE SYNTHESIS
MEDIATED ELECTROPHILIC CYCLIZATION
CONTAINING OXINDOLES
ACTIVATED ALKENES
SODIUM TRIFLUOROMETHANESULFINATE
INTRAMOLECULAR ARYLATION
N-ARYLACRYLAMIDES
ALKYNES
SUBSTITUTED QUINOLINES
TRIFLUOROMETHYLATION
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Summary:An efficient iodocarbocyclization of alkenes for the synthesis of iodooxindoles has been developed. This reaction proceeds in a chemoselective manner and shows excellent tolerance of various functional groups, including a chemosensitive hydroxymethyl group. Nonmetal inorganic iodine pentoxide was used as both the oxidant and iodine source, making this protocol very practical. On the basis of experimental observations, a plausible electrophilic reaction mechanism was proposed.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01130c