Iodine pentoxide-mediated oxidative selenation and seleno/thiocyanation of electron-rich arenes

A simple and efficient method for the regioselective selenation of electron-rich arenes by employing non-metal inorganic iodine pentoxide (I 2 O 5 ) as a reaction promoter under ambient conditions has been developed. The present protocol showed broad functional group tolerance and easy-to-operate an...

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Published inOrganic & biomolecular chemistry Vol. 2; no. 27; pp. 5463 - 5469
Main Authors Wang, Yong-Hao, Zhang, Yun-Qian, Zhou, Chen-Fan, Jiang, You-Qin, Xu, Yue, Zeng, Xiaobao, Liu, Gong-Qing
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 13.07.2022
Royal Society of Chemistry
Subjects
Aromatic compounds
Chemistry
Chemistry, Organic
Functional groups
Iodides
Iodine
Physical Sciences
Salts
Science & Technology
Substitution reactions
Thiocyanates
FUNCTIONALIZATION
SELENOCYANATION
DISELENIDES
ALKENES
INDOLE
BIOLOGICAL EVALUATION
THIOCYANATION
METAL
3-SELENYLINDOLES
MOLECULES
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Summary:A simple and efficient method for the regioselective selenation of electron-rich arenes by employing non-metal inorganic iodine pentoxide (I 2 O 5 ) as a reaction promoter under ambient conditions has been developed. The present protocol showed broad functional group tolerance and easy-to-operate and time-economical features. Additionally, this protocol also allows access to 3-seleno and 3-thiocyanoindoles by the use of readily available selenocyanate and thiocyanate salts. A mechanistic study indicated that the transformation operated through selenenyl iodide-induced electrophilic substitution processes. A simple protocol for the rapid synthesis of chalcogen-containing compounds by an I 2 O 5 -promoted oxidative C sp 2 H selenation and seleno/thiocyanation of activated arenes is reported here.
Bibliography:https://doi.org/10.1039/d2ob00892k
Electronic supplementary information (ESI) available. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00892k