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dc.contributor.authorDooley, Johnathon D.
dc.contributor.authorChidipudi, Suresh Reddy
dc.contributor.authorLam, Hon Wai
dc.date.accessioned2013-08-13T11:08:30Z
dc.date.available2013-08-13T11:08:30Z
dc.date.issued2013-06
dc.identifier.citationearly on-lineen_US
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.urihttp://hdl.handle.net/1842/7671
dc.description.abstractAchieving site-selective, switchable C–H functionalizations of substrates that contain several different types of reactive C–H bonds is an attractive objective to enable the generation of different products from the same starting materials. Herein, we demonstrate the divergent C–H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds that contain two distinct, nonadjacent sites for initial C–H functionalization, where product selectivity is achieved through catalyst control. By use of a palladium–N-heterocyclic carbene complex as the precatalyst, these substrates undergo oxidative annulation with alkynes to provide spiroindenes exclusively. In contrast, a ruthenium-based catalyst system gives benzopyrans as the major products. Examples of divergent, oxidative C–H alkenylations of the same substrates are also provided.en_US
dc.language.isoenen_US
dc.publisherJournal of the American Chemical Societyen_US
dc.subjectAlkenesen_US
dc.titleCatalyst-Controlled Divergent C–H Functionalization of Unsymmetrical 2-Aryl Cyclic 1,3-Dicarbonyl Compounds with Alkynes and Alkenesen_US
dc.typeArticleen_US
dc.identifier.doi10.1021/ja404867k


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