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钯催化一锅法合成2炔基苯并呋喃的研究

Study on One-Pot Synthesis of 2-Ynyl-Benzofuran with Palladium as Catalyst
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摘要 在三乙胺与四氢呋喃混合溶剂中,邻乙炔基苯酚与E-1,2-二碘烯烃在醋酸钯及碘化亚铜的作用下,首先在室温下反应15h,然后在100℃左右继续反应,采用一锅法合成了4种2-炔基苯并呋喃化合物,该方法条件温和且产率较好,产物结构经由NMR和MS确证. Four 2-ynyl-benzofurans were synthesized by the reaction of 2-ethynylaniline and E-1,2-diiodoalkenes in the presence of palladium (II) acetate and copper (I) iodide as the catalysts via a one-pot reaction in a triethylamine-tetrahydrofuran medium. The reaction at room temperature for 15 h and then at 100 ℃ for the remaining time gave the desired 2-ynyl-benzofurans in moderate yields under mild conditions. The structures of the product were characterized and confirmed by MS and NMR spectrum.
出处 《西南大学学报(自然科学版)》 CAS CSCD 北大核心 2010年第9期50-53,共4页 Journal of Southwest University(Natural Science Edition)
基金 湖南省自然科学基金资助项目(08JJ3018) 湖南省教育厅资助项目(08C828)
关键词 一锅法 合成 2-炔基苯并呋喃 one-pot synthesis 2-ynyl-benzofuran
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参考文献11

  • 1汪秋安,丁敏,景明.2-取代芳基苯并呋喃类化合物的合成[J].合成化学,2006,14(2):162-165. 被引量:6
  • 2Nan Y, Miao H, Yang Z. A New Complex of Palladium-Thiourea and Carbon Tetrabromide Catalyzed Carbonylative Annulation of o-Hydroxy-Phenylacetylenes: Efficient New Synthetic Technology for the Synthesis of 2, 3 -Disubtituted Benzo [b] Furans [J]. Org Lett, 2000, 2: 297--299.
  • 3Zeni G, Larock R C. Synthesis of Heteroeycles via Palladium Olefin and Alkyne Chemistry [J]. Chem Rev, 2004, 104(5) : 2285 -- 2310.
  • 4Serra S, Fuganti C. A New Preparative Route to Substituted Dibenzofurans by Benzannulation Reaction. An Application to the Synthesis of Cannabifuran [J]. Synlett, 2003, 13: 2005-2008.
  • 5Miyata O, Takeda N, Naito T. Highly Effective Synthetic Methods for Substituted 2 Arylbenzofurans Using [3, 3] Sigmatropic Rearrangement: Short Syntheses of Stemofuran A and Eupomatenoid 6 [J]. Org Lett, 2004, 6(11): 1761 -- 1763.
  • 6Liang Y, Tao L M, Zhang Y H, et ai. Palladium-Catalyzed Cross Coupling Reactions of 1,2 Diiodo-Alkenes with Terminal Alkynes: Selective Synthesis of Unsymmetrical Buta-1, 3-diynes and 2 Ethynylbenzofurans [J]. Synthesis, 2008, 24:3988- 3994.
  • 7Yue D, Yao T, Larock R C. Synthesis of 2, 3 Disubstituted Benzo [b] Furans by the Palladium-Catalyzed Coupling of olodoanisoles and Terminal Alkynes, Followed by Electrophilic Cyclization [J]. J Org Chem, 2005, 70(25): 10292 -- 10296.
  • 8Hu Y, Nawoschik K J, Liao Y, et al. Synthesis of Conformationally Restricted 2, 3-Diarylbenzo[b]furan by the Pd-Catalyzed Annulation of o-Alkynylphenols: Exploring a Combinatorial Approach [J]. J Org Chem, 2004, 69(7): 2235 -- 2239.
  • 9Flynn B L, Hamel E, Jung M K. One-Pot Synthesis of Benzo [b] Furan and Indole Inhibitors of Tubulin Polymerization [J]. J Med Chem, 2002, 45(12): 2670--2673.
  • 10Hu Y, Zhang Y, Yang Z, et al. Palladium Catalyzed Carbonylative Annulation of o-Alkynylphenols: Syntheses of 2- Substituted-3-aroyl benzo[b]furans [J]. J Org Chem, 2002, 67(7): 2365-2368.

二级参考文献14

  • 1庞冀燕,汪波,陈之朋,许遵乐.2-取代芳基苯并[b]呋喃类化合物的合成[J].有机化学,2005,25(2):176-181. 被引量:11
  • 2Nishiura M, Hou Z M, Wakatauki Y, etal. Novel Z- selective head-to-head dimerization of terminal alkynes catalyzed by lanthanide half-metallocene complexes [J].J Am Chem Soc,2003, 125(5): 1184-1185.
  • 3Grissom J W, Gunawardena G U, Klingderg D. The chemistry enediynes, enyne allenes and related compound [J]. Tetrahedron, 1996, 52 (19). 6453- 6518.
  • 4Li J H, Liu W J, Xie Y X. Recyelable and reuseble Pd ( OAc)2/DABCO/PEG-400 system for suzuki-miyaura cross-coupling reaction [J].J Org Chem, 2005, 70(14): 5409-5412.
  • 5Chandrasehar S, Narsihmulu C H, Sultana S S, et al. Anion recognition and redox sensing amplification by self- assembled monolayers of 1, 1'-bis (alkyl-N-amido) ferrocene [J]. Chem Commun, 2002, (16). 1716- 1717.
  • 6Peruzzini M, Bianchini C, Jia G. Palladium-catalyzed dimerization of terminal alkynes[J]. Organometallics 2005, 24(18): 4330-4332.
  • 7Tomotaka H, Satoshi S, Yasutaka I. Iridium complex-catalyzed cross-coupling reaction of terminal alkynes with internal alkynes via C-H activation of terminal alkynes [J]. Adv Synth Catal, 2005, 347: 872-876.
  • 8Chae S Y, Nianhong L. The ruthenium acetylide catalyzed cross-coupling reaction of terminal and internal alkynes: isolation of a catalytically active aagostic intermediate species [J]. Organometallics, 1998, 17(15). 3158-3160.
  • 9ChenL, Jun C L. Facile and selective copperpalladium catalyzed addition of terminal alkynes to activated alkynes in water [J]. Tetrahedron Lett, 2004, 45(13).2771-2774.
  • 10陶李明,梁云,李金恒.末端炔烃二聚反应合成共轭烯炔的研究进展[J].有机化学,2007,27(9):1078-1086. 被引量:8

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