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Two channels: Cycloalkenes can be selectively functionalized by iridium-catalyzed boronation followed by Suzuki coupling with an aryl iodide or reaction with an aldehyde. The selectivity for allylic and vinylic functionalization can be controlled by a slight change of the reaction conditions. DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, pin=pinacol.
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Olsson et al. (2007) studied this question.
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