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A Pd(0)-Catalyzed Diamination of Terminal Olefins at Allylic and Homoallylic Carbons via Formal C−H Activation under Solvent-Free Conditions
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Abstract
This paper describes a novel diamination process of terminal olefins at allylic and homoallylic carbons via formal C−H activation using di-tert-butyldiaziridinone as nitrogen source and Pd(PPh3)4 as catalyst. A wide variety of terminal olefins can be effectively diaminated in good yields with high stereoselectivity.
Citing Articles
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This article has been cited by 33 ACS Journal articles (5 most recent appear below).
Palladium-Catalyzed Intramolecular Diamination of Acrylic Esters Using Sulfamates as Nitrogen Source
Patricia Chávez, Jonathan Kirsch, Jan Streuff, and Kilian MuñizThe Journal of Organic Chemistry2012 Article ASAPPalladium-Catalyzed Intramolecular Diamination of Acrylic Esters Using Sulfamates as Nitrogen Source
Patricia Chávez, Jonathan Kirsch, Jan Streuff, and Kilian MuñizThe Journal of Organic Chemistry2012 Article ASAPAn intramolecular diamination of acrylates is reported using sulfamates as nitrogen sources. This reaction proceeds under palladium(II) catalysis with copper bromide as oxidant and gives rise to anti-configured 2,3-diamino carboxylates as bicyclic ...
Synthesis of Tricyclic Nitrogen Heterocycles by a Sequence of Palladium-Catalyzed N–H and C(sp3)–H Arylations
Mathieu Guyonnet and Olivier BaudoinOrganic Letters2012 14 (1), 398-401Synthesis of Tricyclic Nitrogen Heterocycles by a Sequence of Palladium-Catalyzed N–H and C(sp3)–H Arylations
Mathieu Guyonnet and Olivier BaudoinOrganic Letters2012 14 (1), 398-401A range of tricyclic nitrogen heterocycles were synthesized in a straightforward and efficient manner via a sequence involving palladium-catalyzed N-arylation and C(sp3)–H arylation as the key steps. Whereas the C(sp3)–H arylation furnished fused 6,5,6-...
Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species
Baoguo Zhao, Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Richard G. Cornwall, and Yian ShiJournal of the American Chemical Society2011 133 (51), 20890-20900Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) Species
Baoguo Zhao, Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Richard G. Cornwall, and Yian ShiJournal of the American Chemical Society2011 133 (51), 20890-20900Conjugated dienes can be diaminated at the internal and/or terminal double bonds using Cu(I) as catalyst and N,N-di-t-butyldiaziridinone (1) as nitrogen source. The regioselectivity is highly dependent upon the choice of Cu(I) catalyst and the ...
New Reactivity of Oxaziridine: Pd(II)-Catalyzed Aromatic C–H Ethoxycarbonylation via C–C Bond Cleavage
Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Baoguo Zhao, and Yian ShiOrganic Letters2011 13 (19), 5244-5247New Reactivity of Oxaziridine: Pd(II)-Catalyzed Aromatic C–H Ethoxycarbonylation via C–C Bond Cleavage
Xingao Peng, Yingguang Zhu, Thomas A. Ramirez, Baoguo Zhao, and Yian ShiOrganic Letters2011 13 (19), 5244-5247A novel Pd(II)-catalyzed aromatic C–H ethoxycarbonylation with oxaziridine involving C–C bond cleavage is described. Various aromatic 2-phenylpyridines and related compounds as well as aryl ureas can be effectively ethoxycarbonylated. A catalytic cycle ...
Molecular Complexity via C–H Activation: A Dehydrogenative Diels–Alder Reaction
Erik M. Stang and M. Christina WhiteJournal of the American Chemical Society2011 Article ASAPMolecular Complexity via C–H Activation: A Dehydrogenative Diels–Alder Reaction
Erik M. Stang and M. Christina WhiteJournal of the American Chemical Society2011 Article ASAPTraditionally, C–H oxidation reactions install oxidized functionality onto a preformed molecular skeleton, resulting in a local molecular change. The use of C–H activation chemistry to construct complex molecular scaffolds is a new area with tremendous ...
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History
- Published In Issue June 20, 2007
- Received March 23, 2007
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