Efficient Electrophilic Cobromination of Alkenes and Bromination of Activated Arenes with Bromodichloroisocyanuric Acid under Mild Conditions
作者:Pierre Esteves、Marcio de Mattos、Leonardo de Almeida
DOI:10.1055/s-2007-982575
日期:2007.7
Efficient methodologies for the preparation of bromodichloroisocyanuric acid were developed (70-75%). This new reagent is very efficient for regioselective electrophilic bromination of activated arenes (86-93%) and cobromination of alkenes with oxygenated nucleophiles (31-98%). The reaction of bromodichloroisocyanuric acid with anisole, acetanilide, N-methylacetanilide leads to 4-substituted monobromoarene and with 2-methoxynaphthalene leads to 1-bromo-2-methoxynaphthalene. Alkenes were cobrominated in the presence of oxygenated nucleophilic solvents (water, alcohols, and acetic acid), leading to the corresponding bromohydrins, β-bromoethers and β-bromoacetates.
开发了高效的方法用于制备溴二氯异氰尿酸(产率70-75%)。这种新试剂在活化芳烃的区域选择性电亲体溴化反应中非常有效(产率86-93%),以及与氧化核苷酸的烯烃共溴化反应中(产率31-98%)。溴二氯异氰尿酸与醇酸、乙酰苯胺和N-甲基乙酰苯胺反应生成4-取代单溴芳烃;与2-甲氧基萘反应生成1-溴-2-甲氧基萘。烯烃在含氧核苷溶剂(如水、醇和醋酸)存在下进行共溴化反应,生成相应的溴醇、β-溴醚和β-溴乙酸酯。