65610-58-4Relevant academic research and scientific papers
Modulating reactivity and diverting selectivity in palladium-catalyzed heteroaromatic direct arylation through the use of a chloride activating/blocking group
Liegault, Benoit,Petrov, Ivan,Gorelsky, Serge I.,Fagnou, Keith
supporting information; experimental part, p. 1047 - 1060 (2010/04/04)
(Chemical Equation Presented) Through the introduction of an aryl chloride substituent, the selectivity of palladium-catalyzed direct arylation may be diverted to provide alternative regioisomeric products in high yields. In cases where low reactivity is typically observed, the presence of the carbon-chlorine bond can serve to enhance reactivity and provide superior outcomes. From a strategic perspective, the C-Cl bond is easily introduced and can be employed in a variety of subsequent transformations to provide a wealth of highly functionalized heterocycles with minimal substrate preactivation. The impact of the C-Cl functional group on direct arylation reactivity has also been evaluated mechanistically, and the observed reactivity profiles correlate very well with that predicted by a concerted metalation-deprotonation pathway.
REACTION OF 3-INDOLYLPHENYLIODONIUM BETAINE WITH ELECTROPHILIC AGENTS
Budylin, V. A.,Ermolenko, M. S.,Chugtai, F. A.,Sharbatyan, P. A.,Kost, A. N.
, p. 1095 - 1097 (2007/10/02)
3-Indolylphenyliodonium chloride and bromide, respectively, were obtained by the action of hydrochloric and hydrobromic acids on 3-indolylphenyliodonium betaine.Pyrolysis of the chloride leads to a mixture of 2- and 3-chloroindoles,while pyrolysis the bromine leads only to 3-bromoindole. 1-Benzyl-2-chloroindole is obtained in the reaction of the betaine with benzyl chloride.The betaine reacts with dimethylsulfate to give an iodonium salt, the reaction of wich with lithium chloride and ammonium chloride leads to 1-methyl-2-chloroindole.
