Steric effect of substituents in haloarenes on the rate of cross-coupling reactions |
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Authors: | T Sh Khaibulova I A Boyarskaya V P Boyarskii |
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Institution: | 1262. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia
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Abstract: | The relative reactivity of ortho- and para-methyl-substituted iodoarenes in the Sonogashira reaction and palladium-catalyzed methoxycarbonylation, as well as of similarly substituted bromoarenes in the Suzuki reactions and cobalt-catalyzed methoxycarbonylation, was studied. Introduction of a methyl group into the para position of aryl halide slows down the cross-coupling. o-Methylhaloarenes are less reactive in palladiumcatalyzed reactions as compared to both unsubstituted haloarene and para-substituted analog. The presence of a methyl group in the ortho position with respect to the reaction center accelerates cobalt-catalyzed methoxycarbonylation. |
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