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Rh催化C-H键活化总结_图文.doc 10页

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Published:January 25,2011 COMMUNICATION /JACS Diverse Strategies toward Indenol and Fulvene Derivatives:Rh-Catalyzed C -H Activation of Aryl Ketones Followed by Coupling with Internal Alkynes Frederic W.Patureau,Tatiana Besset,Nadine Kuhl,and Frank Glorius* Organisch-Chemisches Institut der Westf €a lischen Wilhelms-Universit €a t M €u nster,Corrensstrasse 40,48149M €u nster,Germany b Supporting Information ABSTRACT:The synthesis of indenols and fulvenes was achieved through Rh-catalyzed C -H bond activation of simple and diverse aryl ketone derivatives and subsequent coupling with internal alkynes.The process was found to involve either an R or γdehydration step,depending on the substrate disposition and representing diverse pathways toward functionalized fulvenes. S ince their discovery by Thiele in 1900,1fulvenes and their derivatives have attracted much attention from generations of scientists due to their unique properties in the ?elds of materials science,organometallics and medicinal chemistry.2They are traditionally made by the condensation of cyclopentadienes onto ketones,a method which is typically limited by the availability of the cyclopentadienes,prepared from multistep procedures in which regioselectivity and functional group tolerance are often major di ?culties (eq 1.Likewise,structurally related and biologically relevant indenols also su ?er from limited access,as their preparation usually requires preactivation steps. 3 In modern synthetic chemistry,C -C bond formation through C -H activation reactions has gained importance because it obviates the need for prior activation steps,a pivotal advantage with respect to cost and waste reduction.4The pioneering work on the C -H activation of phenone derivatives,5such as those of Murai,5a Brookhart,5f Cheng,5j and others,5and our recent work on Rh-catalyzed C -H activation of acetophenones 6showed that phenone substrates were suited for ortho C -H functionalization reactions.Herein,we report diverse di

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