Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes

Journal of the Brazilian Chemical Society

Rodrigo Da Silva Ribeiro¹  Pierre M. Esteves¹  Marcio C. S. De Mattos¹ 

[1] ,Universidade Federal do Rio de Janeiro Instituto de Química Rio de Janeiro RJ ,Brazil

关键词: alkenes;    arenes;    electrophilic addition;    electrophilic aromatic substitution;    halogenation;   

DOI  :  10.1590/S0103-50532012000200006

来源: SciELO

【 摘 要 】

Dichloroiodoisocyanuric acid was prepared in 93% by heating trichloroisocyanuric acid with 1.05 mol equiv. of iodine. This new reagent is very efficient for regioselective electrophilic iodination of activated arenes. Alkenes react with dichloroiodoisocyanuric acid in the presence of oxygenated nucleophiles (water, alcohols, and acetic acid), leading to the corresponding iodohydrins, β-iodoethers and β-iodoacetates with reaction times of less than one minute and with a high degree of regioselectivity. Enol ethers resulted in the regioselective formation of the corresponding iodine-dialkylacetals. Experimental results and DFT calculations showed that dichoroiodoisocyanuric acid is more reactive with unsaturated systems than triiodoisocyanuric acid.

【 授权许可】

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