Palladium/Imadazolium Salt Mediated Cyclisations for the Synthesis of Heterocyclic Compounds
Affiliation(s)
1 Centre for Drug Design and Development, Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana. 2 Centre for Biomolecular Design and Drug Development, The Chemistry Laboratory, CPES, University of Sussex, Brighton, UK. 3 Department of Chemistry, University College London, London, UK.
1 Centre for Drug Design and Development, Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana. 2 Centre for Biomolecular Design and Drug Development, The Chemistry Laboratory, CPES, University of Sussex, Brighton, UK. 3 Department of Chemistry, University College London, London, UK.
ABSTRACT
The use of intramolecular reactions involving palladium/imidazolium salts to synthesize hetero-cyclic compounds is described. Reactivity of phenyl, ethyl and methyl substituents leading to isolation of various isomeric products is also illustrated. Rearrangement of phenyl intermediates to furnish benzoxazoles is also mentioned.
The use of intramolecular reactions involving palladium/imidazolium salts to synthesize hetero-cyclic compounds is described. Reactivity of phenyl, ethyl and methyl substituents leading to isolation of various isomeric products is also illustrated. Rearrangement of phenyl intermediates to furnish benzoxazoles is also mentioned.
KEYWORDS
N-Heterocyclic Carbenes, Heterocyclic Systems, Imidazolium Salt, Intramolecular Cyclicsations, Phosphine Ligands
N-Heterocyclic Carbenes, Heterocyclic Systems, Imidazolium Salt, Intramolecular Cyclicsations, Phosphine Ligands
Cite this paper
Kofie, W. , Caddick, S. (2015) Palladium/Imadazolium Salt Mediated Cyclisations for the Synthesis of Heterocyclic Compounds. International Journal of Organic Chemistry, 5, 223-231. doi: 10.4236/ijoc.2015.54022.
Kofie, W. , Caddick, S. (2015) Palladium/Imadazolium Salt Mediated Cyclisations for the Synthesis of Heterocyclic Compounds. International Journal of Organic Chemistry, 5, 223-231. doi: 10.4236/ijoc.2015.54022.
References
[1] Belestkaya, I.P. and Cheprakov, A.V. (2000) The Heck Reaction as a Sharpening Stone of Palladium Catalysis. Chemical Reviews, 100, 3009-3066.
http://dx.doi.org/10.1021/cr9903048 [2] Oestreich, M., Dennison, P.R., Kodanko, J.J. and Overman, L.E. (2001) Thwarting β-Hydride Elimination: Capture of the Alkylpalladium Intermediate of an Asymmetric Intramolecular Heck Reaction. Angewandte Chemie International Edition, 40, 1439-1442.
http://dx.doi.org/10.1002/1521-3773(20010417)40:8<1439::AID-ANIE1439>3.0.CO;2-F [3] Tsuji, J. (1997) Palladium Reagents and Catalyst; Innovations in Organic in Organic Synthesis. Wiley & Sons. [4] Alcazar-Roman, L.M. and Hartwig, J.F. (2001) Mechanism of Aryl Chloride Amination:? Base-Induced Oxidative Addition. Journal of the American Chemical Society, 123, 12905-12906.
http://dx.doi.org/10.1021/ja016491k [5] Alcazar-Roman, L.M. and Hartwig, J.F. (2002) Mechanistic Studies on Oxidative Addition of Aryl Halides and Triflates to Pd(BINAP)2 and Structural Characterization of the Product from Aryl Triflate Addition in the Presence of Amine. Organometallics, 21, 491-502.
http://dx.doi.org/10.1021/om0108088 [6] Muci, A.R. and Buchwald, S.L. (2002) Practical Palladium Catalysts for C-N and C-O Bond Formation. Topics in Current Chemistry, 219, 131-201.
http://dx.doi.org/10.1007/3-540-45313-X_5 [7] Northeton, M.R. and Fu, G.C. (2001) Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes. Organic Letters, 3, 4295-4298.
http://dx.doi.org/10.1021/ol016971g [8] Herrmann, W.A., Weskamp, T. and Bohm, V.P.W. (2002) Metal Complexes of Stable Carbenes. Advances in Organometallic Chemistry, 48, 1-69.
http://dx.doi.org/10.1016/S0065-3055(01)48001-4 [9] Bohm, V.P.W., Gstottmayr, C.W.K., Westkamp, T. and Herman, W.A. (2000) N-Heterocyclic Carbenes: Part 26. N-Heterocyclic Carbene Complexes of Palladium(0): Synthesis and Application in the Suzuki Cross-Coupling Reaction. Journal of Organometallic Chemistry, 596, 186-190.
http://dx.doi.org/10.1016/S0022-328X(99)00590-2 [10] Staueeer, S.R., Lee, S., Sambuli, J.P., Hauck, S.I. and Hartwig, J.F. (2000) High Turnover Number and Rapid, Room-Temperature Amination of Chloroarenes Using Saturated Carbene Ligands. Organic Letters, 2, 1423-1426.
http://dx.doi.org/10.1021/ol005751k [11] Huang, J., Grasa, G. and Nolan, S.P. (1999) General and Efficient Catalytic Amination of Aryl Chlorides Using a Palladium/Bulky Nucleophilic Carbene System. Organic Letters, 1, 1370-1309.
http://dx.doi.org/10.1021/ol990987d [12] Grundeman, S., Albrecht, M., Kovacevic, A., Faller, J.W. and Crabtree, R.H. (2002) Bis-Carbene Complexes from Oxidative Addition of Imidazolium C-H Bonds to Pal-ladium(0). Journal of the Chemical Society, Dalton Transactions, 2163-2167.
http://dx.doi.org/10.1039/b110964b [13] Igau, A., Grutzmacher, H., Baceiredo, A. and Bertrand, G. (1988) Analogous α,α’-Bis-Carbenoid, Triply Bonded Species: Synthesis of a Stable λ3-Phosphinocarbene-λ5-Phosphaacetylene. Journal of the American Chemical Society, 110, 6463-6466.
http://dx.doi.org/10.1021/ja00227a028 [14] Caddick, S. and Kofie, W. (2002) Observations on the Intramolecular Heck Reactions of Aromatic Chlorides Using Palladium/Imidazolium Salts. Tet-rahedron Letters, 43, 9347-9350.
http://dx.doi.org/10.1016/S0040-4039(02)02340-7 [15] Menicagli, R., Malanga, C., Dell’Innocenti, M. and Lardicci, L. (1987) Triisobutylaluminum-Assisted Reductive Rearrangement of Alkyl 1-Alkenyl Acetals: An Easy Synthesis of β-Alkoxy Alcohols. The Journal of Organic Chemistry, 52, 5700-5704.
http://dx.doi.org/10.1021/jo00235a010 [16] Kaiwar, V., Rees, C.B., Gray, E.J. and Neidle, S. (1995) Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine. Journal of the Chemical Society, Perkin Transactions, 2281-2288.
http://dx.doi.org/10.1039/p19950002281 [17] Eremeev, A.V., Polyak, F.D., Vosekalna, I.A., Chervin, I.I., Nasibov, S.S. and Kostyanovskii, R.G. (1984) Absolute Configuration of Diastereomeric Derivatives of N-Substituted Aziridine-2-Carboxylic Acids. Chemistry of Heterocyclic Compounds, 20, 1102-1107.
http://dx.doi.org/10.1007/BF00503598 [18] Bankston, D., Fang, F., Huie, E. and Xie, S. (1999) Palladium(II) Acetate-Tris(triphenylphosphine)rhodium(I) Chloride: A Novel Catalytic Couple for the Intramolecular Heck Reaction. The Journal of Organic Chemistry, 64, 3461- 3466.
http://dx.doi.org/10.1021/jo982058q [19] Marimoto, K., Hirano, K., Sato, T. and Miura, M. (2011) Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes. The Journal of Organic Chemistry, 76, 9548-9551.
http://dx.doi.org/10.1021/jo201923d [20] Giles, R.G.F., Rickards, R.W. and Senanayake, S.B. (1998) Synthesis of Isochroman-3-Ylacetates and Isochromane- γ-Lactones through Rearrangement of Aryldioxolanylacetates. Journal of the Chemical Society, Perkin Transactions, 3949-3956.
http://dx.doi.org/10.1039/a807005i [21] Young, D.W. (2010) Synthetic Chemistry: An Upfront Investment. Nature Chemical Biology, 6, 174-175.
http://dx.doi.org/10.1038/nchembio.325 [22] Terashima, M. and Ishii, M. (1982) A Facile Synthesis of 2-Substituted Benzoxazoles. Synthesis, 1982, 484-485.
http://dx.doi.org/10.1055/s-1982-29847 [23] Minami, T., Isonaka, T., Okada, Y. and Ichikawa, J. (1993) Copper(I) Salt-Mediated Arylation of Phosphinyl-Stabi- lized Carbanions and Synthetic Application to Heterocyclic Compounds. The Journal of Organic Chemistry, 58, 7009-7015.
http://dx.doi.org/10.1021/jo00077a018 [24] Park, H.J., Park, M.S., Lee, T.H. and Park, K.H. (2013) Synthesis of 2-Styrylbenzoxazole Derivatives by the Reaction of Styrylphenolic Schiff Bases with Thianthrene Cation Radical. Journal of Heterocyclic Chemistry, 50, 663-667.
http://dx.doi.org/10.1002/jhet.1707
[1] Belestkaya, I.P. and Cheprakov, A.V. (2000) The Heck Reaction as a Sharpening Stone of Palladium Catalysis. Chemical Reviews, 100, 3009-3066.
http://dx.doi.org/10.1021/cr9903048 [2] Oestreich, M., Dennison, P.R., Kodanko, J.J. and Overman, L.E. (2001) Thwarting β-Hydride Elimination: Capture of the Alkylpalladium Intermediate of an Asymmetric Intramolecular Heck Reaction. Angewandte Chemie International Edition, 40, 1439-1442.
http://dx.doi.org/10.1002/1521-3773(20010417)40:8<1439::AID-ANIE1439>3.0.CO;2-F [3] Tsuji, J. (1997) Palladium Reagents and Catalyst; Innovations in Organic in Organic Synthesis. Wiley & Sons. [4] Alcazar-Roman, L.M. and Hartwig, J.F. (2001) Mechanism of Aryl Chloride Amination:? Base-Induced Oxidative Addition. Journal of the American Chemical Society, 123, 12905-12906.
http://dx.doi.org/10.1021/ja016491k [5] Alcazar-Roman, L.M. and Hartwig, J.F. (2002) Mechanistic Studies on Oxidative Addition of Aryl Halides and Triflates to Pd(BINAP)2 and Structural Characterization of the Product from Aryl Triflate Addition in the Presence of Amine. Organometallics, 21, 491-502.
http://dx.doi.org/10.1021/om0108088 [6] Muci, A.R. and Buchwald, S.L. (2002) Practical Palladium Catalysts for C-N and C-O Bond Formation. Topics in Current Chemistry, 219, 131-201.
http://dx.doi.org/10.1007/3-540-45313-X_5 [7] Northeton, M.R. and Fu, G.C. (2001) Air-Stable Trialkylphosphonium Salts: Simple, Practical, and Versatile Replacements for Air-Sensitive Trialkylphosphines. Applications in Stoichiometric and Catalytic Processes. Organic Letters, 3, 4295-4298.
http://dx.doi.org/10.1021/ol016971g [8] Herrmann, W.A., Weskamp, T. and Bohm, V.P.W. (2002) Metal Complexes of Stable Carbenes. Advances in Organometallic Chemistry, 48, 1-69.
http://dx.doi.org/10.1016/S0065-3055(01)48001-4 [9] Bohm, V.P.W., Gstottmayr, C.W.K., Westkamp, T. and Herman, W.A. (2000) N-Heterocyclic Carbenes: Part 26. N-Heterocyclic Carbene Complexes of Palladium(0): Synthesis and Application in the Suzuki Cross-Coupling Reaction. Journal of Organometallic Chemistry, 596, 186-190.
http://dx.doi.org/10.1016/S0022-328X(99)00590-2 [10] Staueeer, S.R., Lee, S., Sambuli, J.P., Hauck, S.I. and Hartwig, J.F. (2000) High Turnover Number and Rapid, Room-Temperature Amination of Chloroarenes Using Saturated Carbene Ligands. Organic Letters, 2, 1423-1426.
http://dx.doi.org/10.1021/ol005751k [11] Huang, J., Grasa, G. and Nolan, S.P. (1999) General and Efficient Catalytic Amination of Aryl Chlorides Using a Palladium/Bulky Nucleophilic Carbene System. Organic Letters, 1, 1370-1309.
http://dx.doi.org/10.1021/ol990987d [12] Grundeman, S., Albrecht, M., Kovacevic, A., Faller, J.W. and Crabtree, R.H. (2002) Bis-Carbene Complexes from Oxidative Addition of Imidazolium C-H Bonds to Pal-ladium(0). Journal of the Chemical Society, Dalton Transactions, 2163-2167.
http://dx.doi.org/10.1039/b110964b [13] Igau, A., Grutzmacher, H., Baceiredo, A. and Bertrand, G. (1988) Analogous α,α’-Bis-Carbenoid, Triply Bonded Species: Synthesis of a Stable λ3-Phosphinocarbene-λ5-Phosphaacetylene. Journal of the American Chemical Society, 110, 6463-6466.
http://dx.doi.org/10.1021/ja00227a028 [14] Caddick, S. and Kofie, W. (2002) Observations on the Intramolecular Heck Reactions of Aromatic Chlorides Using Palladium/Imidazolium Salts. Tet-rahedron Letters, 43, 9347-9350.
http://dx.doi.org/10.1016/S0040-4039(02)02340-7 [15] Menicagli, R., Malanga, C., Dell’Innocenti, M. and Lardicci, L. (1987) Triisobutylaluminum-Assisted Reductive Rearrangement of Alkyl 1-Alkenyl Acetals: An Easy Synthesis of β-Alkoxy Alcohols. The Journal of Organic Chemistry, 52, 5700-5704.
http://dx.doi.org/10.1021/jo00235a010 [16] Kaiwar, V., Rees, C.B., Gray, E.J. and Neidle, S. (1995) Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine. Journal of the Chemical Society, Perkin Transactions, 2281-2288.
http://dx.doi.org/10.1039/p19950002281 [17] Eremeev, A.V., Polyak, F.D., Vosekalna, I.A., Chervin, I.I., Nasibov, S.S. and Kostyanovskii, R.G. (1984) Absolute Configuration of Diastereomeric Derivatives of N-Substituted Aziridine-2-Carboxylic Acids. Chemistry of Heterocyclic Compounds, 20, 1102-1107.
http://dx.doi.org/10.1007/BF00503598 [18] Bankston, D., Fang, F., Huie, E. and Xie, S. (1999) Palladium(II) Acetate-Tris(triphenylphosphine)rhodium(I) Chloride: A Novel Catalytic Couple for the Intramolecular Heck Reaction. The Journal of Organic Chemistry, 64, 3461- 3466.
http://dx.doi.org/10.1021/jo982058q [19] Marimoto, K., Hirano, K., Sato, T. and Miura, M. (2011) Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes. The Journal of Organic Chemistry, 76, 9548-9551.
http://dx.doi.org/10.1021/jo201923d [20] Giles, R.G.F., Rickards, R.W. and Senanayake, S.B. (1998) Synthesis of Isochroman-3-Ylacetates and Isochromane- γ-Lactones through Rearrangement of Aryldioxolanylacetates. Journal of the Chemical Society, Perkin Transactions, 3949-3956.
http://dx.doi.org/10.1039/a807005i [21] Young, D.W. (2010) Synthetic Chemistry: An Upfront Investment. Nature Chemical Biology, 6, 174-175.
http://dx.doi.org/10.1038/nchembio.325 [22] Terashima, M. and Ishii, M. (1982) A Facile Synthesis of 2-Substituted Benzoxazoles. Synthesis, 1982, 484-485.
http://dx.doi.org/10.1055/s-1982-29847 [23] Minami, T., Isonaka, T., Okada, Y. and Ichikawa, J. (1993) Copper(I) Salt-Mediated Arylation of Phosphinyl-Stabi- lized Carbanions and Synthetic Application to Heterocyclic Compounds. The Journal of Organic Chemistry, 58, 7009-7015.
http://dx.doi.org/10.1021/jo00077a018 [24] Park, H.J., Park, M.S., Lee, T.H. and Park, K.H. (2013) Synthesis of 2-Styrylbenzoxazole Derivatives by the Reaction of Styrylphenolic Schiff Bases with Thianthrene Cation Radical. Journal of Heterocyclic Chemistry, 50, 663-667.
http://dx.doi.org/10.1002/jhet.1707