Reference : Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homo...
Scientific journals : Article
Physical, chemical, mathematical & earth Sciences : Chemistry
http://hdl.handle.net/2268/81744
Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium-arene complexes
English
Borguet, Yannick mailto [Université de Liège - ULg > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique >]
Sauvage, Xavier [Université de Liège - ULg > > Centre de recherches du cyclotron >]
Zaragoza, Guillermo [> > > >]
Demonceau, Albert mailto [Université de Liège - ULg > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique >]
Delaude, Lionel mailto [Université de Liège - ULg > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique >]
2010
Beilstein Journal of Organic Chemistry
Beilstein-Institut
6
1167-1173
Yes (verified by ORBi)
International
1860-5397
Frankfurt am Main
Germany
[en] Grubbs catalyst ; indenylidene ligands ; Kharasch reaction ; microwave heating ; olefin metathesis
[en] The tandem catalysis of ring-closing metathesis/atom transfer radical reactions was investigated with the homobimetallic ruthenium-indenylidene complex [(p-cymene)Ru(mu-Cl)(3)RuCl(3-phenyl-1-indenylidene)(PCy3)] (1) to generate active species in situ. The two catalytic processes were first carried out independently in a case study before the whole sequence was optimized and applied to the synthesis of several polyhalogenated bicyclic gamma-lactams and lactones from alpha,omega-diene substrates bearing trihaloacetamide or trichloroacetate functionalities. The individual steps were carefully monitored by H-1 and P-31 NMR spectroscopies in order to understand the intimate details of the catalytic cycles. Polyhalogenated substrates and the ethylene released upon metathesis induced the clean transformation of catalyst precursor 1 into the Ru(II)-Ru(III) mixed-valence compound [(p-cymene) Ru(mu-Cl)(3)RuCl2(PCy3)], which was found to be an efficient promoter for atom transfer radical reactions under the adopted experimental conditions.
Researchers ; Professionals
http://hdl.handle.net/2268/81744
10.3762/bjoc.6.133

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