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Intramolecular C−H Amination Reactions: Exploitation of the Rh2(II)-Catalyzed Decomposition of Azidoacrylates
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Abstract
Rhodium(II) perfluorobutyrate-mediated decomposition of vinyl azides provides a new, mild entry into Rh2(II) nitrenoid chemistry. This methodology allows rapid access to a variety of complex, functionalized N-heterocycles in two steps from commercially available starting materials.
Citing Articles
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This article has been cited by 35 ACS Journal articles (5 most recent appear below).
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Francisco Velázquez, Srikanth Venkatraman, Charles A. Lesburg, José Duca, Stuart B. Rosenblum, Joseph A. Kozlowski, and F. George NjorogeOrganic Letters2012 14 (2), 556-559The synthesis of substituted 3,4-dihydrofuranoindoles is reported. These new indole compounds were used to synthesize potent HCV NS5B inhibitors. The binding mode of the dihydrofuranoindole-derived inhibitors was established via X-ray crystallographic ...
Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones
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Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen WangOrganic Letters2011 13 (24), 6362-6365A highly efficient and convenient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles from readily accessible 2-azido acrylates and nitrones has been developed. This reaction proceeded under mild conditions without the assistance of any metal, ...
Highly Efficient Synthesis of Quinoxalinone-N-oxide via Tandem Nitrosation/Aerobic Oxidative C–N Bond Formation
Yusuke Kobayashi, Mami Kuroda, Natsuki Toba, Mari Okada, Rie Tanaka, and Tetsutaro KimachiOrganic Letters2011 13 (23), 6280-6283Highly Efficient Synthesis of Quinoxalinone-N-oxide via Tandem Nitrosation/Aerobic Oxidative C–N Bond Formation
Yusuke Kobayashi, Mami Kuroda, Natsuki Toba, Mari Okada, Rie Tanaka, and Tetsutaro KimachiOrganic Letters2011 13 (23), 6280-6283An efficient method for constructing quinoxalinone-N-oxides from cyanoacetanilides has been developed. This transformation can be achieved using inexpensive reagents and molecular oxygen under mild conditions, thus offering a practical pathway to ...
A Diruthenium Catalyst for Selective, Intramolecular Allylic C–H Amination: Reaction Development and Mechanistic Insight Gained through Experiment and Theory
Mark Edwin Harvey, Djamaladdin G. Musaev, and J. Du BoisJournal of the American Chemical Society2011 133 (43), 17207-17216A Diruthenium Catalyst for Selective, Intramolecular Allylic C–H Amination: Reaction Development and Mechanistic Insight Gained through Experiment and Theory
Mark Edwin Harvey, Djamaladdin G. Musaev, and J. Du BoisJournal of the American Chemical Society2011 133 (43), 17207-17216The mixed-valent paddlewheel complex tetrakis(2-oxypyridinato)diruthenium(II,III) chloride, [Ru2(hp)4Cl], catalyzes intramolecular allylic C–H amination with bis(homoallylic) sulfamate esters. These results stand in marked contrast to reactions performed ...
Mechanism of Cobalt(II) Porphyrin-Catalyzed C−H Amination with Organic Azides: Radical Nature and H-Atom Abstraction Ability of the Key Cobalt(III)-Nitrene Intermediates
Volodymyr Lyaskovskyy , Alma I. Olivos Suárez , Hongjian Lu , Huiling Jiang , X. Peter Zhang , and Bas de BruinJournal of the American Chemical Society 0 (ja),Mechanism of Cobalt(II) Porphyrin-Catalyzed C−H Amination with Organic Azides: Radical Nature and H-Atom Abstraction Ability of the Key Cobalt(III)-Nitrene Intermediates
Volodymyr Lyaskovskyy , Alma I. Olivos Suárez , Hongjian Lu , Huiling Jiang , X. Peter Zhang , and Bas de BruinJournal of the American Chemical Society 0 (ja),The mechanism of cobalt(II) porphyrin-catalyzed benzylic C–H bond amination of ethylbenzene, toluene and 1,2,3,4-tetrahydronaphthalene (tetralin) with a series of different organic azides as nitrene sources was studied by means of DFT calculations and EPR ...
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History
- Published In Issue June 20, 2007
- Received March 29, 2007
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