基于芳基炔烃的钯催化环化反应以及碘参与的亲电环化反应的研究
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摘要
基于炔烃环化反应一直是有机合成化学的研究热点之一,以此为基础,在
新型荧光材料的设计和合成,药物分子的设计与合成等学科前沿领域里都有着极为广泛的应用。本论文主要综述了基于炔烃的金属钯催化的环化反应和碘参与的亲电环化反应,并在此基础上,重点研究了以下的内容：
1.以1,8-二碘萘和炔醇为原料,通过钯催化环化的一锅法合成方法,依次活化了sp、sp2、sp3类型的C-H键,最终有效地构建了一蒽酮环,并成功地将其应用到氟离子的荧光传感上。(对应于论文第二章第一节)2.以1,8-二炔基萘和脂肪／芳香胺为原料,在空气氛围下,以PdCl2为催化剂,DMSO做溶剂,有效地构建了一厄烯并吡咯环,并将其应用到硝基化合物荧光传感上。(对应于论文第二章第二节)
3.以邻卤代苯乙酮和炔烃为原料,通过反应条件的控制,在不同的Pd催化剂和反应溶剂之下,可以有效地构建了p-氨基荼和茚酮环,并将β-氨基荼应用到氢离子的荧光传感上。(对应于论文第二章第三节)
4.以二芳基乙炔和芳香胺为原料,通过反应条件的控制,在不同的反应溶剂中,可以有效地构建了2,3-二芳基吲哚和1,2,3,4,5-五芳基吡咯环,并提出了相应的反应机理。(对应于论文第二章第四节)
5.以1,8-二炔基取代荼为原料,经由碘参与的亲电环化反应,通过对反应底物和溶剂的控制,可以有效地合成一系列新颖的稠环分子,例如荧蒽环、茚并蒽环、厄烯并环戊二烯环、氮杂荧蒽等,并借助理论计算的手段,提出了它们各自的周环反应机理。(对应于论文第三章)
The cyclization based on alkyne is one of the hottest research topics in organic synthetic chemistry, and it has been widely applied in many frontier areas such as design and synthesis of novel fluorescent materials and medical molecules, etc. In this thesis, the research background of palladium-catalyzed cyclization of alkyne and the iodine-mediated electronphilic cyclization of alkyne is reviewed, and the details of my study are listed as follows:
1. Phenalenone derivatives were synthesized via palladium catalyzed bicyclization of1,8-diiodonaphthalene and tertiary propargylic alcohols in an one-pot reaction, the activations of sp,sp2and sp3C-H bonds were included in this reaction. Moreover, the resulting phenalenones could be successfully applied as a potential fluorescent chemosensor for fluoride anion with high sensitivity and selectivity,(see Section1, Chapter2in this thesis)
2.8H-Acenaphtho[1,2-c]pyrrole derivatives could be successfully constructed from1,8-diarenynyl naphthalenes and amines. The reaction was conducted under air atmosphere, PdCl2as catalyst and DMSO as reaction solvent. Moreover, the resulting8H-Acenaphtho[1,2-c]pyrroles could be applied as a potential fluorescent chemosensor for trace explosive detection,(see Section2, Chapter2in this thesis)
3. β-Dialkylaminonaphthalenes and indenes could be effectively constructed from o-haloacetophenones and terminal alkynes under the control of the Pd catalysts and reaction solvents. Moreover, the β-dialkylaminonaphthalenes could be applied as a potential fluorescent chemosensor for environmental acidity (see Section3, Chapter2in this thesis)
4.2,3-Diarylindone and pentaarylpyrrole were respectively constructed from diarylacetylene and arylamine effectively via the control of the reaction solvent in the presence of palladium (Ⅱ) chloride,(see Section4, Chapter2in this thesis)
5. Four different types of fused arenes, including fluoranthene, indeno[2,1-a] phenalene,8H-cyclopenta[a]acenaphthylene, and pyridine[a]acenaphthylene were easily and efficiently constructed via iodine-mediated electrophilic cyclizations of different1,8-dialkynyl naphthalene derivatives in a special solvent,(see Chapter3in this thesis)
新型荧光材料的设计和合成,药物分子的设计与合成等学科前沿领域里都有着极为广泛的应用。本论文主要综述了基于炔烃的金属钯催化的环化反应和碘参与的亲电环化反应,并在此基础上,重点研究了以下的内容：
1.以1,8-二碘萘和炔醇为原料,通过钯催化环化的一锅法合成方法,依次活化了sp、sp2、sp3类型的C-H键,最终有效地构建了一蒽酮环,并成功地将其应用到氟离子的荧光传感上。(对应于论文第二章第一节)2.以1,8-二炔基萘和脂肪／芳香胺为原料,在空气氛围下,以PdCl2为催化剂,DMSO做溶剂,有效地构建了一厄烯并吡咯环,并将其应用到硝基化合物荧光传感上。(对应于论文第二章第二节)
3.以邻卤代苯乙酮和炔烃为原料,通过反应条件的控制,在不同的Pd催化剂和反应溶剂之下,可以有效地构建了p-氨基荼和茚酮环,并将β-氨基荼应用到氢离子的荧光传感上。(对应于论文第二章第三节)
4.以二芳基乙炔和芳香胺为原料,通过反应条件的控制,在不同的反应溶剂中,可以有效地构建了2,3-二芳基吲哚和1,2,3,4,5-五芳基吡咯环,并提出了相应的反应机理。(对应于论文第二章第四节)
5.以1,8-二炔基取代荼为原料,经由碘参与的亲电环化反应,通过对反应底物和溶剂的控制,可以有效地合成一系列新颖的稠环分子,例如荧蒽环、茚并蒽环、厄烯并环戊二烯环、氮杂荧蒽等,并借助理论计算的手段,提出了它们各自的周环反应机理。(对应于论文第三章)
The cyclization based on alkyne is one of the hottest research topics in organic synthetic chemistry, and it has been widely applied in many frontier areas such as design and synthesis of novel fluorescent materials and medical molecules, etc. In this thesis, the research background of palladium-catalyzed cyclization of alkyne and the iodine-mediated electronphilic cyclization of alkyne is reviewed, and the details of my study are listed as follows:
1. Phenalenone derivatives were synthesized via palladium catalyzed bicyclization of1,8-diiodonaphthalene and tertiary propargylic alcohols in an one-pot reaction, the activations of sp,sp2and sp3C-H bonds were included in this reaction. Moreover, the resulting phenalenones could be successfully applied as a potential fluorescent chemosensor for fluoride anion with high sensitivity and selectivity,(see Section1, Chapter2in this thesis)
2.8H-Acenaphtho[1,2-c]pyrrole derivatives could be successfully constructed from1,8-diarenynyl naphthalenes and amines. The reaction was conducted under air atmosphere, PdCl2as catalyst and DMSO as reaction solvent. Moreover, the resulting8H-Acenaphtho[1,2-c]pyrroles could be applied as a potential fluorescent chemosensor for trace explosive detection,(see Section2, Chapter2in this thesis)
3. β-Dialkylaminonaphthalenes and indenes could be effectively constructed from o-haloacetophenones and terminal alkynes under the control of the Pd catalysts and reaction solvents. Moreover, the β-dialkylaminonaphthalenes could be applied as a potential fluorescent chemosensor for environmental acidity (see Section3, Chapter2in this thesis)
4.2,3-Diarylindone and pentaarylpyrrole were respectively constructed from diarylacetylene and arylamine effectively via the control of the reaction solvent in the presence of palladium (Ⅱ) chloride,(see Section4, Chapter2in this thesis)
5. Four different types of fused arenes, including fluoranthene, indeno[2,1-a] phenalene,8H-cyclopenta[a]acenaphthylene, and pyridine[a]acenaphthylene were easily and efficiently constructed via iodine-mediated electrophilic cyclizations of different1,8-dialkynyl naphthalene derivatives in a special solvent,(see Chapter3in this thesis)
引文
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[45]For recent reviews on indole-containing natural products, see:(a) M. Somei, F. Yamada, Simple indole alkaloids and those with a nonrearranged monoterpenoid unit, Nat. Prod. Rep., 2004,21,278-311; (b) M. Somei, F. Yamada, Simple indole alkaloids and those with a non-rearranged monoterpenoid unit, Nat. Prod. Rep.,2005,22,73-103; (c) A. J. Kochanowska-Karamyan, T. Mark, M. J. Hamann, Marine Indole Alkaloids:Potential New Drug Leads for the Control of Depression and Anxiety, Chem. Rev.,2010,110,4489-4497.
[46]a) S. Wurtz, S. Rakshit, J. J. Neumann, T. Droge, F. Glorius, Palladium-Catalyzed Oxidative Cyclization of N-Aryl Enamines:From Anilines to Indoles, Angew. Chem. Int. Ed.,2008,47, 7230-7233; b) J. J. Neumann, S. Rakshit, T. Droge, S. Wurtz, F. Glorius, Exploring the Oxidative Cyclization of Substituted N-Aryl Enamines:Pd-Catalyzed Formation of Indoles from Anilines, Chem. Eur. J.,2011,17,7298-7303.
[47]D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, Indole Synthesis via Rhodium Catalyzed Oxidative Coupling of Acetanilides and Internal Alkynes, J. Am. Chem. Soc., 2008,130,16474-16475.
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[1]For reviews of iodocyclization, see:a) A. N. French, S. Bissmire, T. Wirth, Iodine electrophiles in stereoselective reactions:recent developments and synthetic applications, Chem. Soc. Rev., 2004,33,354-362; b) R. C. Larock, Acetylene Chemistry, Eds, F. Diederich, P. J. Stang, R. R. Tykwinski, Wiley-VCH; Weinheim, Germany:2005,51-99; c) H. Togo, S. Iida, Synthetic Use of Molecular Iodine for Organic Synthesis, Synlett,2006,2159-2175.
[2]For selected examples, see:a) J. Barluenga, M. Trincado, E. Rubio, J. M. Gonzalez, IPy2BF4-Promoted Intramolecular Addition of Masked and Unmasked Anilines to Alkynes:Direct Assembly of 3-Iodoindole Cores, Angew. Chem. Int. Ed., 2003,42,2406-2409; b) D. Yue, R. C. Larock, Synthesis of 3-Iodoindoles by Electrophilic Cyclization of N,N-Dialkyl-2-(1-alkynyl)anilines, Org. Lett.,2004,6,1037-1040; c) K. O. Hessian, B. L. Flynn, Selective endo and exo Iodocyclizations in the Synthesis of Quinolines and Indoles, Org. Lett.,2006,8,243-246; d) R. Halim, P. J. Scammells, B. L. Flynn, Org. Lett.,2008,10,1967; e) T. Okitsu, K. Sato, A. Wada, Reagent-Controlled Oxidative Aromatization in Iodocyclization:Switchable Access to Dihydropyrazoles and Pyrazoles, Org. Lett.,2010,12,3506-3509; f) H.-C. Ouyang, R.-Y. Tang, P. Zhong, X.-G. Zhang, J.-H. Li, CuI/I2-Promoted Electrophilic Tandem Cyclization of 2-Ethynylbenzaldehydes with ortho-Benzenediamines:Synthesis of Iodoisoquinoline-Fused Benzimidazoles, J. Org. Chem.,2011,76,223-228.
[3]For selected examples, see:a) J. Barluenga, H. Vazquez-Villa, I. Merino, A. Ballesteros, J. M. Gonzalez, The Reaction of o-Alkynylarene and Heteroarene Carboxaldehyde Derivatives with Iodonium Ions and Nucleophiles:A Versatile and Regioselective Synthesis of 1H-Isochromene, Naphthalene, Indole, Benzofuran, and Benzothiophene Compounds, Chem. Eur. J.,2006,12, 5790-5805; b) Z. W. Just, R. C. Larock, Synthesis of 2(3H)-Furanones via Electrophilic Cyclization, J. Org. Chem.,2008,73,2662-2667; c) S. Arimitsu, J. M. Jacobsen, G. B. Hammond, Synthesis of 2,4,5-Trisubstituted 3-Fluorofurans via Sequential Iodocyclization and Cross-Coupling of gem-Difluorohemopropargyl Alcohols, J. Org. Chem.,2008,73,2886; d) K.-G. Ji, H.-T. Zhu, F. Yang, A. Shaukat, X.-F. Xia, Y.-F. Yang, X.-Y. Liu, Y.-M. Liang, Synthesis of Five-and Six-Membered Dihalogenated Heterocyclic Compounds by Electrophile-Triggered Cyclization, J. Org. Chem.,2010,75,5670-5678; e) A. K. Verma, T. Aggarwal, V. Rustagi, R. C. Larock, Iodine-catalyzed and solvent-controlled selective electrophilic cyclization and oxidative esterification of ortho-alkynyl aldehydes, Chem. Commun.,2010,46,4064-4066.
[4]For selected examples, see:a) B. L. Flynn, P. Verdier-Pinard, E. Hamel, A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[b]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents, Org. Lett.,2001,3,651-654; b) K. O. Hessian, B. L. Flynn, Iodine-Induced Reaction Cascades for the Rapid Construction of Variously Substituted Benzothiophenes, Org. Lett.,2003,5,4377-4380; c) C. T. Bui, B. L. Flynn, Solid-Phase Synthesis of 2,3-Disubstituted Benzo[b]thiophenes and Benzo[b]selenophenes, J. Comb. Chem.,2006,8,163-167; d) C.-H. Cho, D.-I Jung, R. C. Larock, A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b] thiophenes prepared via iodocyclization, Tetrahedron Lett.,2010,51,6485-6488.
[5]For selected examples, see:a) T. Kesharwani, S. A. Worlikar, R. C. Larock, Synthesis of 2,3-Disubstituted Benzo[b]selenophenes via Electrophilic Cyclization, J. Org. Chem.,2006,71, 2307-2312; b) D. Alves, C. Luchese, C. W. Nogueira, G. Zeni, Electrophilic Cyclization of (Z)-Selenoenynes:Synthesis and Reactivity of 3-Iodoselenophenes, J. Org. Chem.,2007,72, 6726-6734; c) D. R. Garud, M. Koketsu, Synthesis of 3-Selena-l-dethiacephems and Selenazepines via Iodocyclization, Org. Lett.,2008,10,3319-3322.
[6]For selected examples, see:a) T. Yao, M. A. Campo, R. C. Larock, Synthesis of Polycyclic Aromatic Iodides via IC1-Induced Intramolecular Cyclization, Org. Lett.,2004,6,2677-2680; b) J. Barluenga, M. Trincado, M. Marco-Arias, A. Ballesteros, E. Rubio, J. M. Gonzalez, Intramolecular iodoarylation reaction of alkynes:easy access to derivatives of benzofused heterocycles, Chem. Commun.,2005,2008-2010; c) X. Zhang, S. Sarkar, R. C. Larock, Synthesis of Naphthalenes and 2-Naphthols by the Electrophilic Cyclization of Alkynes, J. Org. Chem., 2006,71,236-243; d) J. Barluenga, M. Trincado, E. Rubio, J. M. Gonzalez, Direct Intramolecular Arylation of Aldehydes Promoted by Reaction with IPy2BF4/HBF4:Synthesis of Benzocyclic Ketones,Angew. Chem. Int. Ed.,2006,45,3140-3143; e) S. A. Worlikar, T. Kesharwani, T. Yao, R. C. Larock, Synthesis of 3,4-Disubstituted 2H-Benzopyrans through C-C Bond Formation via Electrophilic Cyclization, J. Org. Chem.,2007,72,1347-1353; f) X. Zhang, T. Yao, M. A. Campo, R. C. Larock, Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines, Tetrahedron,2010,66,1177-1187; g) B. Crone, S. F. Kirsch, K.-D. Umland, Electrophilic Cyclization of 1,5-Enynes, Angew. Chem. Int. Ed.,2010,49,4661-4664.
[7]a) Q.-F. Yu, Y.-H. Zhang, Q. Yin, B.-X. Tang, R.-Y. Tang, P. Zhong, J.-H. Li, Electrophilic ipso-Iodocyclization of N-(4-Methylphenyl)propiolamides:Selective Synthesis of 8-Methyleneazaspiro[4,5]trienes, J. Org. Chem.,2008,73,3658-3661; b) B.-X. Tang, D.-J. Tang, S. Tang, Q.-F. Yu, Y.-H. Zhang, Y. Liang, P. Zhong, J.-H. Li, Selective Synthesis of Spiro[4,5]trienyl Acetates via an Intramolecular Electrophilic ipso-Iodocyclization Process, Org.Lett.,2008,10,1063-1066; c) T. Okitsu, D. Nakazawa, A. Kobayashi, M. Mizohata, Y. In, T. Ishida, A. Wada,ipso-Iodocyclization of Ethoxyethyl Ethers to Alkynes at the ortho-Position:An Efficient Synthesis of Functionalized Spiro Compounds, Synlett,2010,203-206.
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[42]For recent reviews on the synthesis of indole, see:(a) G. W. Gribble, Recent developments in indole ring synthesis-methodology and Applications, J. Chem. Soc.,Perkin Trans.1,2000, 1045-1075; (b) S. Cacchi, G. Fabrizi, Synthesis and Functionalization of Indoles Through Palladium-catalyzed Reactions, Chem. Rev.,2005,105,2873-2920; (c) G. R. Humphrey, J. T. Kuethe, Practical Methodologies for the Synthesis of Indoles, Chem. Rev.,2006,106,2875-2911. For selective individual accounts, see:(d) M. Shen, B. E. Leslie, T. G. Driver, Dirhodium(II)-Catalyzed Intramolecular C-H Amination of Aryl Azides, Angew. Chem. Int. Ed., 2008,47,5056-5059; (e) O. Leogane, H. Lebel, One-Pot Multicomponent Synthesis of Indoles from 2-Iodobenzoic Acid, Angew. Chem. Int. Ed.,2008,47,350-352; (f) K. Alex, A. Tillack, N. Schwarz, M. Beller, Zinc-Promoted Hydrohydrazination of Terminal Alkynes:An Efficient Domino Synthesis of Indoles, Angew. Chem. Int. Ed,2008,47,2304-2307; (g) J. Takaya, S. Udagawa, H. Kusama, N. Iwasawa, Synthesis of N-Fused Tricyclic Indoles by a Tandem [1,2] Stevens-Type Rearrangement/1,2-Alkyl Migration of Metal-Containing Ammonium Ylides, Angew. Chem. Int. Ed.,2008,47,4906-4909; (h) T. Pei, C. Chen, P. G. Dormer, I. W. Davies, Expanding the [1,2]-Aryl Migration to the Synthesis of Substituted Indoles, Angew. Chem. Int. Ed., 2008,47,4231-4233; (i) S. Cacchi, G. Fabrizi, A. Goggiamani, A. Perboni, A. Sferrazza, P. Stabile, 2,3-Disubstituted Indoles via Palladium-Catalyzed Reaction of 2-Alkynyltrifluoroacetanilides with Arenediazonium Tetrafluoroborates, Org. Lett.,2010,12,3279-3281.
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[1]For reviews of iodocyclization, see:a) A. N. French, S. Bissmire, T. Wirth, Iodine electrophiles in stereoselective reactions:recent developments and synthetic applications, Chem. Soc. Rev., 2004,33,354-362; b) R. C. Larock, Acetylene Chemistry, Eds, F. Diederich, P. J. Stang, R. R. Tykwinski, Wiley-VCH; Weinheim, Germany:2005,51-99; c) H. Togo, S. Iida, Synthetic Use of Molecular Iodine for Organic Synthesis, Synlett,2006,2159-2175.
[2]For selected examples, see:a) J. Barluenga, M. Trincado, E. Rubio, J. M. Gonzalez, IPy2BF4-Promoted Intramolecular Addition of Masked and Unmasked Anilines to Alkynes:Direct Assembly of 3-Iodoindole Cores, Angew. Chem. Int. Ed., 2003,42,2406-2409; b) D. Yue, R. C. Larock, Synthesis of 3-Iodoindoles by Electrophilic Cyclization of N,N-Dialkyl-2-(1-alkynyl)anilines, Org. Lett.,2004,6,1037-1040; c) K. O. Hessian, B. L. Flynn, Selective endo and exo Iodocyclizations in the Synthesis of Quinolines and Indoles, Org. Lett.,2006,8,243-246; d) R. Halim, P. J. Scammells, B. L. Flynn, Org. Lett.,2008,10,1967; e) T. Okitsu, K. Sato, A. Wada, Reagent-Controlled Oxidative Aromatization in Iodocyclization:Switchable Access to Dihydropyrazoles and Pyrazoles, Org. Lett.,2010,12,3506-3509; f) H.-C. Ouyang, R.-Y. Tang, P. Zhong, X.-G. Zhang, J.-H. Li, CuI/I2-Promoted Electrophilic Tandem Cyclization of 2-Ethynylbenzaldehydes with ortho-Benzenediamines:Synthesis of Iodoisoquinoline-Fused Benzimidazoles, J. Org. Chem.,2011,76,223-228.
[3]For selected examples, see:a) J. Barluenga, H. Vazquez-Villa, I. Merino, A. Ballesteros, J. M. Gonzalez, The Reaction of o-Alkynylarene and Heteroarene Carboxaldehyde Derivatives with Iodonium Ions and Nucleophiles:A Versatile and Regioselective Synthesis of 1H-Isochromene, Naphthalene, Indole, Benzofuran, and Benzothiophene Compounds, Chem. Eur. J.,2006,12, 5790-5805; b) Z. W. Just, R. C. Larock, Synthesis of 2(3H)-Furanones via Electrophilic Cyclization, J. Org. Chem.,2008,73,2662-2667; c) S. Arimitsu, J. M. Jacobsen, G. B. Hammond, Synthesis of 2,4,5-Trisubstituted 3-Fluorofurans via Sequential Iodocyclization and Cross-Coupling of gem-Difluorohemopropargyl Alcohols, J. Org. Chem.,2008,73,2886; d) K.-G. Ji, H.-T. Zhu, F. Yang, A. Shaukat, X.-F. Xia, Y.-F. Yang, X.-Y. Liu, Y.-M. Liang, Synthesis of Five-and Six-Membered Dihalogenated Heterocyclic Compounds by Electrophile-Triggered Cyclization, J. Org. Chem.,2010,75,5670-5678; e) A. K. Verma, T. Aggarwal, V. Rustagi, R. C. Larock, Iodine-catalyzed and solvent-controlled selective electrophilic cyclization and oxidative esterification of ortho-alkynyl aldehydes, Chem. Commun.,2010,46,4064-4066.
[4]For selected examples, see:a) B. L. Flynn, P. Verdier-Pinard, E. Hamel, A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[b]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents, Org. Lett.,2001,3,651-654; b) K. O. Hessian, B. L. Flynn, Iodine-Induced Reaction Cascades for the Rapid Construction of Variously Substituted Benzothiophenes, Org. Lett.,2003,5,4377-4380; c) C. T. Bui, B. L. Flynn, Solid-Phase Synthesis of 2,3-Disubstituted Benzo[b]thiophenes and Benzo[b]selenophenes, J. Comb. Chem.,2006,8,163-167; d) C.-H. Cho, D.-I Jung, R. C. Larock, A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b] thiophenes prepared via iodocyclization, Tetrahedron Lett.,2010,51,6485-6488.
[5]For selected examples, see:a) T. Kesharwani, S. A. Worlikar, R. C. Larock, Synthesis of 2,3-Disubstituted Benzo[b]selenophenes via Electrophilic Cyclization, J. Org. Chem.,2006,71, 2307-2312; b) D. Alves, C. Luchese, C. W. Nogueira, G. Zeni, Electrophilic Cyclization of (Z)-Selenoenynes:Synthesis and Reactivity of 3-Iodoselenophenes, J. Org. Chem.,2007,72, 6726-6734; c) D. R. Garud, M. Koketsu, Synthesis of 3-Selena-l-dethiacephems and Selenazepines via Iodocyclization, Org. Lett.,2008,10,3319-3322.
[6]For selected examples, see:a) T. Yao, M. A. Campo, R. C. Larock, Synthesis of Polycyclic Aromatic Iodides via IC1-Induced Intramolecular Cyclization, Org. Lett.,2004,6,2677-2680; b) J. Barluenga, M. Trincado, M. Marco-Arias, A. Ballesteros, E. Rubio, J. M. Gonzalez, Intramolecular iodoarylation reaction of alkynes:easy access to derivatives of benzofused heterocycles, Chem. Commun.,2005,2008-2010; c) X. Zhang, S. Sarkar, R. C. Larock, Synthesis of Naphthalenes and 2-Naphthols by the Electrophilic Cyclization of Alkynes, J. Org. Chem., 2006,71,236-243; d) J. Barluenga, M. Trincado, E. Rubio, J. M. Gonzalez, Direct Intramolecular Arylation of Aldehydes Promoted by Reaction with IPy2BF4/HBF4:Synthesis of Benzocyclic Ketones,Angew. Chem. Int. Ed.,2006,45,3140-3143; e) S. A. Worlikar, T. Kesharwani, T. Yao, R. C. Larock, Synthesis of 3,4-Disubstituted 2H-Benzopyrans through C-C Bond Formation via Electrophilic Cyclization, J. Org. Chem.,2007,72,1347-1353; f) X. Zhang, T. Yao, M. A. Campo, R. C. Larock, Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines, Tetrahedron,2010,66,1177-1187; g) B. Crone, S. F. Kirsch, K.-D. Umland, Electrophilic Cyclization of 1,5-Enynes, Angew. Chem. Int. Ed.,2010,49,4661-4664.
[7]a) Q.-F. Yu, Y.-H. Zhang, Q. Yin, B.-X. Tang, R.-Y. Tang, P. Zhong, J.-H. Li, Electrophilic ipso-Iodocyclization of N-(4-Methylphenyl)propiolamides:Selective Synthesis of 8-Methyleneazaspiro[4,5]trienes, J. Org. Chem.,2008,73,3658-3661; b) B.-X. Tang, D.-J. Tang, S. Tang, Q.-F. Yu, Y.-H. Zhang, Y. Liang, P. Zhong, J.-H. Li, Selective Synthesis of Spiro[4,5]trienyl Acetates via an Intramolecular Electrophilic ipso-Iodocyclization Process, Org.Lett.,2008,10,1063-1066; c) T. Okitsu, D. Nakazawa, A. Kobayashi, M. Mizohata, Y. In, T. Ishida, A. Wada,ipso-Iodocyclization of Ethoxyethyl Ethers to Alkynes at the ortho-Position:An Efficient Synthesis of Functionalized Spiro Compounds, Synlett,2010,203-206.
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[9]a) P. R. Schreiner, M. Prall, V. Lutz, Fulvenes from Enediynes:Regioselective Electrophilic Domino and Tandem Cyclizations of Enynes and Oligoynes, Angew. Chem. Int. Ed.,2003,42, 5757-5760; b) S. V. Kovalenko, S. Peabody, M. Manoharan, R. J. Clark, I. V. Alabugin, 5-Exo-dig Radical Cyclization of Enediynes:The First Synthesis of Tin-Substituted Benzofulvenes, Org. Lett.,2004,6,2457-2460.
[10]a) C. Zhang, D.-M. Cui, L.-Y. Yao, B.-S. Wang, Y.-Z. Hu, T. Hayashi, Synthesis of 2-Cyclohexenone Derivatives via Gold(I)-Catalyzed Hydrative Cyclization of 1,6-Diynes, J. Org. Chem.,2008,73,7811-7813; b) Y. Matano, M. Nakashima, H. Imahori, A Convenient Method for the Synthesis of a-Ethynylphospholes and Modulation of Their π-Conjugated Systems, Angew. Chem. Int. Ed.,2009,48,4002-4005; c) P. A. Wender, J. P. Christy, A. B. Lesser, M. T. Gieseler, The Synthesis of Highly Substituted Cyclooctatetraene Scaffolds by Metal-Catalyzed [2+2+2+2] Cycloadditions:Studies on Regioselectivity, Dynamic Properties, and Metal Chelation, Angew. Chem. Int. Ed.,2009,48,7687-7690; d) S. Garcia-Rubin, J. A. Varela, L. Castedo, C. Sad,6πe-versus 8πe-Electrocyclization of 1-Aryl-and Heteroaryl-Substituted (1Z,3Z)-1,3,5-Hexatrienes:A Matter of Aromaticity, Org. Lett.,2009,11,983-986;e) M. Hapke, K. Kral, C. Fischer, A. Spannenberg, A. Gutnov, D. Redkin, B. Heller, 1-Aryl-5,6,7,8-tetrahydroquinolines by Cobalt-Catalyzed [2+2+2] Cycloaddition Reaction of 1-Aryl-1,7-octadiynes and Nitriles, J. Org. Chem.,2010,75,3993-4003.
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[1]For the synthesis of 1,8-diiodonaphthalene, see:H. House, D. Koepsell, W. J. Campbell, The Synthesis of Some Diphenyl and Triphenyl Derivatives of Anthracene and Naphthalene, J. Org. Chem.,1972,37,1003-1011.
[2]For the synthesis of propynols, see:Z. Lu, S. Ma, Studies on the Cu(Ⅰ)-Catalyzed Regioselective anti-Carbometallation of Secondary Terminal Propargylic Alcohols, J. Org. Chem.,2006,71,2655-2660.
[3]R. Chinchilla, C. Najera, The Sonogashira Reaction:A Booming Methodology in Synthetic Organic Chemistry, Chem. Rev.,2007,107,874-922.
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