Phase-Transfer-Catalyzed Intramolecular Hydroaryloxylation and Hydroamination of C≡C Triple Bonds: An Efficient Synthesis of Benzo[b]furan and 3-Methyleneisoindoline-1-one Derivatives
ABSTRACT
Phase-transfer-catalyzed intramolecular cyclization reaction of forming benzo[b]furan and 3-methyleneisoin- doline-1-one derivatives has been developed. The cyclization reaction of propargylic carbonates was also de- scribed under metal-free condition and the reaction was reported by Pd and Ni before. The reaction condi- tions and the scope of the process are examined. The catalysts are cheap and environmentally friendly and the substrates are readily available and the procedure is simple, rapid, and general. The development of C-O and C-N bond formation processes via an overall structural isomerization represents the most atom-eco- nomical approach.
Phase-transfer-catalyzed intramolecular cyclization reaction of forming benzo[b]furan and 3-methyleneisoin- doline-1-one derivatives has been developed. The cyclization reaction of propargylic carbonates was also de- scribed under metal-free condition and the reaction was reported by Pd and Ni before. The reaction condi- tions and the scope of the process are examined. The catalysts are cheap and environmentally friendly and the substrates are readily available and the procedure is simple, rapid, and general. The development of C-O and C-N bond formation processes via an overall structural isomerization represents the most atom-eco- nomical approach.
Cite this paper
nullJ. Hu, L. Liu, X. Wang, Y. Hu, S. Yang and Y. Liang, "Phase-Transfer-Catalyzed Intramolecular Hydroaryloxylation and Hydroamination of C≡C Triple Bonds: An Efficient Synthesis of Benzo[b]furan and 3-Methyleneisoindoline-1-one Derivatives," Green and Sustainable Chemistry, Vol. 1 No. 4, 2011, pp. 165-169. doi: 10.4236/gsc.2011.14025.
nullJ. Hu, L. Liu, X. Wang, Y. Hu, S. Yang and Y. Liang, "Phase-Transfer-Catalyzed Intramolecular Hydroaryloxylation and Hydroamination of C≡C Triple Bonds: An Efficient Synthesis of Benzo[b]furan and 3-Methyleneisoindoline-1-one Derivatives," Green and Sustainable Chemistry, Vol. 1 No. 4, 2011, pp. 165-169. doi: 10.4236/gsc.2011.14025.
References
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[1] T. E. Müller and M. Beller, “Metal-Initiated Amination of Alkenes and Alkynes,” Chemical Reviews, Vol. 98, No. 2, 1998, pp. 675-704. doi:10.1021/cr960433d [2] J. H. Teles, S. Brode and M. Chabanas, “Cationic Gold(I) Complexes Highly Efficient Catalysts for the Addition of Alcohols to Alkynes,” Angewandte Chemie International Edition, Vol. 37, No. 10, 1998, pp. 1415-1418. doi:10.1002/(SICI)1521-3773(19980605)37:10<1415::AID-ANIE1415>3.0.CO;2-N [3] Y. Yamamoto and U. Radhakrishnan, “Palladium Catalysed Pronucleophile Addition to Unactivated Carbon-Carbon Multiple Bonds,” Chemical Society Reviews, Vol. 28, No. 3, 1999, pp. 199-207. doi:10.1039/a806581k [4] F. Pohlki and S. Doye, “The Catalytic Hydroamination of Alkynes,” Chemical Society Reviews, Vol. 32, No. 2, 2003, pp. 104-114. doi:10.1039/b200386b [5] F. Alonso, I. P. Beletskaya and M. Yus, “Transition-Me- tal-Catalyzed Addition of Heteroatom-Hydrogen Bonds to Alkynes,” Chemical Reviews, Vol. 104, No. 6, 2004, pp. 3079-3160. doi:10.1021/cr0201068 [6] D. K. Barange, T. C. Nishad, N. K. Swamy, V. Bandameedi, D. Kumar, B. R. Sreekanth, K. Vyas and M. Pal, “A Remarkable Accelerating Effect of Ag-Salt on Intra-molecular Cyclization of o-(1-Alkynyl)benzenesulfona- nmides,” The Journal of Organic Chemistry, Vol. 72, No. 22, 2007, pp. 8547-8550. doi:10.1021/jo701470h [7] Y. Yu, A. Gregory, G. A. Stephenson and D. Mitchell, “A Regioselective Synthesis of 3-Benzazepinones via Intramolecular Hydroamidation of Acetylenes,” Tetrahedron Letters, Vol. 47, No. 23, 2006, pp. 3811-3814. doi:10.1016/j.tetlet.2006.03.198 [8] X. L. Hou, Z. Yang, K. S. Yeung and H. N. C. Wong, “In Progress in Heterocyclic Chemistry,” In: G. W. Gribble and J. A. Joule, Eds., Elsevier, Oxford, 2008; Vol. 19, pp. 176-207. [9] B. Carlsson, B. N. Singh, M. Temciuc, S. Nilsson, Y.-L. Li, C. Mellin and J. Malm, “Synthesis and Preliminary Characterization of a Novel Antiarrhythmic Compound (KB130015) with an Improved Toxicity Profile Compared with Amiodarone” Journal of Medicinal Chemistry, Vol. 45, No. 3, 2002, pp. 623-630. doi:10.1021/jm001126+ [10] B. L. Flynn, E. Hamel and M. K. Jung, “One-Pot Synthesis of Benzo[b]furan and Indole Inhibitors of Tubulin Polymerization,” Journal of Medicinal Chemistry, Vol. 45, No. 12, 2002, pp. 2670-2673. doi:10.1021/jm020077t [11] F. Alonso, I. P. Beletskaya and M. Yus, “Transition-Metal-Catalyzed Addition of Heteroatom-Hydrogen Bonds to Al- kynes,” Chemical Reviews, Vol. 104, No. 6, 2004, pp. 3079- 3160. doi:10.1021/cr0201068 [12] G. Zeni and R. C. Larock, “Synthesis of Heterocycles via Palladium-Catalyzed Oxidative Addition,” Chemical Re- views, Vol. 106, No. 11, 2006, pp. 4644-4680. [13] A. S. K. Hashmi, T. M. Frost and J. W. Bats, “Gold Catalysis: On the Phenol Synthesis,” Organic. Letters, Vol. 3, No. 23, 2001, pp. 3769-3771. doi:10.1021/ol016734d [14] M. Carril, R. SanMartin, I. Tellitu and E. Dominguez, “On-Water Chemistry: Copper-Catalyzed Straightforward Synthesis of Benzo[b]furan Derivatives in Neat Water,” Organic Letters, Vol. 8, No. 7, 2006, pp. 1467-1470. doi:10.1021/ol060274c. [15] B. Zhao and X. Lu, “Cationic Palladium(II)-Catalyzed Addition of Arylboronic Acids to Nitriles. One-Step Synthesis of Benzofurans from Phenoxyacetonitriles,” Organic Letters, Vol. 8, No. 26, 2006, pp. 5987-5990. [16] J. Hu, X.-C. Wang, L.-N. Guo, Y.-Y. Hu, X.-Y. Liu and Y.-M. Liang, “Pd/C-Catalyzed Cyclization/Isomerization: A New Route to 2-Aroyl-3-vinyl benzo[b]furans via Carbon-Carbon Bond Formation,” Catalysis Communications, Vol. 5, No. 25, 2010, pp. 346-350. doi:10.1016/j.catcom.2009.10.028 [17] G. Blaskó, D. J. Gula and M. Shamma, “The Phthalideisoquinoline Alkaloids,” Journal of Naturral Products, Vol. 45, No. 2, 2010, pp. 105-122. [18] N. G. Kundu and M. W. Khan, “Palladium-Catalysed Heteroannulation with Terminal Alkynes: a Highly Regio- and Stereoselective Synthesis of (Z)-3-Aryl(alkyl) idene Isoindolin-1-ones,” Tetrahedron Letters, Vol. 56, No. 27, 2000, pp. 4777-4792. [19] E. V. Dehmlow and S. S. Dehmlow, “Phase Transfer Catalysis,” 3rd Edition, VCH, Weinheim, 1993. [20] C. M. Starks, C. L. Liotta and M. Halpern, “Phase-Transfer Catalysis” Chapman & Hall, New York, 1994. doi:10.1007/978-94-011-0687-0 [21] Y. Sasson and R. Neumann, “Handbook of Phase-Transfer Catalysis” Blackie Academic & Professional, London, 1997. doi:10.1007/978-94-009-0023-3 [22] M. E. Halpern, “Phase-Transfer Catalysis; ACS Symposium Series 659,” American Chemical Society, Washington, D.C., 1997. [23] J. Hu, L.-Y. Wu, X.-C. Wang, Y.-Y. Hu, Y.-N. Niu, X.-Y. Liu, S. Yang and Y.-M. Liang, “Phase-Transfer-Cata- lyzed Intramolecular Cyclization of ortho-Alkynyl Phenyl Ether Derivatives for Synthesis of 2,3-Disubstituted Ben- zo[b]furans,” Advanced. Synthesis &. Catalysis, Vol. 352, No. 2-3, 2010, pp. 351-356. [24] H.-P. Bi, X.-Y. Liu, F.-R. Gou, L.-N. Guo, X.-H, Duan and Y.-M. Liang, “Highly Regioselective Synthesis of Indene Derivatives Including an Allene Functional Group via Pd/C-Catalyzed Cyclization Reaction in Air,” Organic. Letters, Vol. 9, No. 18, 2007, pp. 3527-3529. doi:10.1021/ol071385u [25] F.-R. Gou, H.-P. Bi, L.-N. Guo, Z.-H. Guan, X.-Y. Liu and Y.-M. Liang, “New Insight into Ni(II)-Catalyzed Cyclization Reactions of Propargylic Compounds with Soft Nucleophiles: Novel Indenes Formation,” The Journal of Organic Chemistry, Vol. 73, No. 10, 2008, pp. 3837-3841. doi:10.1021/jo800155a [26] Y. Shi, J. Huang, Y.-F. Yang, L.-Y. Wu, Y.-N. Niu, P.-F. Huo, X.-Y. Liu and Y.-M. Liang, “One-Pot Synthesis of Highly Substituted Allenylidene Derivatives via Palladium- or Nickel-Catalyzed Tandem Michael Addition– Cyclization Reaction,” Advanced. Synthesis &. Catalysis, Vol. 351, No. 1-2, 2009, pp. 141-146.