A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles, pyrroles, pyrazoles, and azaindoles were synthesized from the corresponding bromoalkyl azole and an aryl iodide.
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A novel one-step synthesis of imidazo[5,1-a]isoquinolines via a tandem Pd-catalyzed alkylation-direct arylation sequence.
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February 2009
School of Chemistry, University College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran.
A palladium-catalyzed/norbornene-mediated one-step synthesis of highly functionalized imidazoles via a sequential alkyl-aryl and aryl-heteroaryl bond formation is devised. This method provides an efficient route to a wide variety of substituted imidazo[5,1-a]isoquinolines from readily accessible N-bromoalkyl imidazoles and aryl iodides.
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Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6, Canada.
A variety of six-membered-ring annulated 2H-indazoles and 1,2,3- and 1,2,4-triazoles were synthesized in good to excellent yields from the corresponding bromoethyl azoles and aryl iodides. The annulation process involves a one-pot norbornene-mediated palladium-catalyzed sequence whereby an alkyl-aryl bond and an aryl-heteroaryl bond are successively formed through two C-H bond activations. Subsequent functionalizations of the resulting polycyclic through cross-coupling reactions are also presented.
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Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada.
A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles, pyrroles, pyrazoles, and azaindoles were synthesized from the corresponding bromoalkyl azole and an aryl iodide.
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Org Lett
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Davenport Laboratories, Chemistry Department, University of Toronto, Ontario, Canada.
[reaction: see text] A palladium-catalyzed/norbornene-mediated sequential coupling reaction involving an aromatic sp(2) C-H functionalization as the key step is described, in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one pot. A variety of highly substituted six- and seven-membered annulated pyrroles and pyrazoles were synthesized in a one-step process in good yields from readily accessible N-bromoalkyl pyrroles or pyrazoles and aryl iodides.
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J Am Chem Soc
September 2005
Davenport Laboratories, Chemistry Department, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
A norbornene-mediated palladium-catalyzed tandem alkylation/C-H functionalization sequence is described, in which an alkyl-aryl bond and a heteroaryl-aryl bond are formed in one pot. A variety of highly substituted six- and seven-membered ring annulated indoles were synthesized in good yields from bromoalkyl indoles and aryl iodides.
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