An efficient Rh -catalyzed direct C2-alkenylation of indoles using readily available potassium vinyltrifluoroborate under mild conditions has been developed. This protocol features wide substrate scope and excellent functional group compatibility, enabling a facile access to diverse terminal vinylindoles in moderate to good yields. Furthermore, the C2-alkenylated indole can be easily transformed into 9H-carbazole through a ring-closing metathesis/aromatization cascade.
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Catalytic Cycloisomerization onto a Carbonyl Oxygen.
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Department of Chemistry, Columbia University, 3000 Broadway, New York New York, 10027, United States.
We have found that terminal -vinylindoles bearing cycloalkanone substituents are excellent hydrogen atom acceptors, generating α-aminyl radicals with a variety of catalysts (Co(II)/H or Co(III)Cl precatalysts with silane reductants). These radicals can be converted to internal vinylindoles but eventually add to the oxygen of the cycloalkanone substituents. These cyclizations eventually furnish a densely functionalized dihydrofuran (a net cycloisomerization).
View Article and Find Full Text PDFSynthesis of Terminal Vinylindoles via Rh -Catalyzed Direct C-H Alkenylation with Potassium Vinyltrifluoroborate.
Chemistry
April 2018
Key Laboratory of Optoelectronic Chemical Materials and Devices, Ministry of Education, School of Chemical, Environmental Engineering, Jianghan University, 8 Sanjiaohu Road, Wuhan, 430056, China.
An efficient Rh -catalyzed direct C2-alkenylation of indoles using readily available potassium vinyltrifluoroborate under mild conditions has been developed. This protocol features wide substrate scope and excellent functional group compatibility, enabling a facile access to diverse terminal vinylindoles in moderate to good yields. Furthermore, the C2-alkenylated indole can be easily transformed into 9H-carbazole through a ring-closing metathesis/aromatization cascade.
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Chem Commun (Camb)
December 2016
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Meilong Road No. 130, Shanghai 200237, China and State Key Laboratory of Organometallic Chemistry, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as the terminal oxidant through β-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to obtain a series of 2- and 3-vinylindoles which are important synthetic intermediates in many natural indole derivatives.
View Article and Find Full Text PDFGold(III)-catalyzed double hydroamination of o-alkynylaniline with terminal alkynes leading to N-vinylindoles.
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Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA.
A highly efficient double-hydroamination reaction of o-alkynylanilines with terminal alkynes leading to N-alkenylindoles was developed by using gold(III) as a catalyst under neat conditions. [reaction: see text].
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Org Lett
May 2005
Department of Chemistry, University of Rochester, New York 14627-0216, USA.
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