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Synthesis of Carbazoles and Dibenzofurans via Cross-Coupling of o-Iodoanilines and o-Iodophenols with Silylaryl Triflates
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Abstract
An efficient route to synthesize a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. This chemistry tolerates a variety of functional groups.
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This article has been cited by 18 ACS Journal articles (5 most recent appear below).
Cu-Catalyzed Oxidative C(sp2)–H Cycloetherification of o-Arylphenols for the Preparation of Dibenzofurans
Jiaji Zhao, Yong Wang, Yimiao He, Lanying Liu, and Qiang ZhuOrganic Letters2012 Article ASAPCu-Catalyzed Oxidative C(sp2)–H Cycloetherification of o-Arylphenols for the Preparation of Dibenzofurans
Jiaji Zhao, Yong Wang, Yimiao He, Lanying Liu, and Qiang ZhuOrganic Letters2012 Article ASAPA new process involving copper-catalyzed aerobic C(sp2)–H activation, followed by cycloetherification, has been developed. This reaction serves as a direct method for the preparation of multisubstituted dibenzofurans starting with o-arylphenols. The ...
Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
Yuesi Fang, Chunrui Wu, Richard C. Larock, and Feng ShiThe Journal of Organic Chemistry2011 76 (21), 8840-8851Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
Yuesi Fang, Chunrui Wu, Richard C. Larock, and Feng ShiThe Journal of Organic Chemistry2011 76 (21), 8840-8851A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed ...
Gold-Catalyzed Deacylative Cycloisomerization Reactions of 3-Acylindole/ynes: A New Approach for Carbazole Synthesis
Lu Wang, Guijie Li, and Yuanhong LiuOrganic Letters2011 13 (15), 3786-3789Gold-Catalyzed Deacylative Cycloisomerization Reactions of 3-Acylindole/ynes: A New Approach for Carbazole Synthesis
Lu Wang, Guijie Li, and Yuanhong LiuOrganic Letters2011 13 (15), 3786-3789The synthesis of functionalized carbazoles through gold-catalyzed deacylative cycloisomerization of 3-acylindole/ynes is described. A mechanistic proposal for these transformations involving a novel carbonyl group facilitated heterolytic fragmentation ...
Synthesis of Dihydrobenzisoxazoles by the [3 + 2] Cycloaddition of Arynes and Oxaziridines
Arif Kivrak and Richard C. LarockThe Journal of Organic Chemistry2010 75 (21), 7381-7387Synthesis of Dihydrobenzisoxazoles by the [3 + 2] Cycloaddition of Arynes and Oxaziridines
Arif Kivrak and Richard C. LarockThe Journal of Organic Chemistry2010 75 (21), 7381-7387Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C−O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and ...
One-Pot Synthesis of New Substituted 1,2,3,4-Tetrahydrocarbazoles via Petasis Reaction
Subhasish Neogi, Amrita Roy, and Dinabandhu NaskarJournal of Combinatorial Chemistry2010 12 (5), 617-629One-Pot Synthesis of New Substituted 1,2,3,4-Tetrahydrocarbazoles via Petasis Reaction
Subhasish Neogi, Amrita Roy, and Dinabandhu NaskarJournal of Combinatorial Chemistry2010 12 (5), 617-629The one-pot synthesis of a new substituted 1,2,3,4-tetrahydrocarbazoles has been described via Petasis reactions. These tetrahydrocarbazoles exhibits various medicinal importance and might be suitable for elaboration into larger peptides at carboxy ...
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History
- Published In Issue October 14, 2004
- Received July 23, 2004
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