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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 8
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Original Articles

Vicinal Difunctionalization of Alkynyl Selenides with Lithium Butylcyano Cuprate and Electrophiles

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Pages 1165-1170 | Received 21 Jul 1993, Published online: 23 Sep 2006

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Read on this site (8)

ClaudioC. Silveira, Paula Boeck, MauroL. Begnini & AntonioL. Braga. (2001) A Convenient Synthesis of Phenyl 1-Chloro-1 Alkenyl Chalcogenides by One-Pot Wittig Reaction. Synthesis of Selenolesters. Phosphorus, Sulfur, and Silicon and the Related Elements 172:1, pages 173-179.
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C.C. Silveira, C.S. Botega, C.R. B. Rhoden, M.R. S. Nunes, A.L. Braga & E.J. Lenardão. (1998) A Facile Synthesis of α-Phenylchalcogeno(S, Se) α,β-Unsaturated Esters from Ethyl α-Bromo-α-phenylchalcogeno Acetates. Synthetic Communications 28:18, pages 3371-3380.
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HélioA. Stefani, Nicola Petragnani, JoãoV. Comasseto, AntônioL. Braga & PauloH. Menezes. (1998) Highly Functionalized Selenocyclopropanes From 1-Halo-1-Chalcogeno Alkenes. Synthetic Communications 28:9, pages 1667-1677.
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Jun-Lian Zhang & Zhen-Chu Chen. (1997) Hypervalent Iodine in Synthesis XXV: An Effective Synthesis of Acetylenic Selenides via Alkynylphenyliodonium Tosylates. Synthetic Communications 27:21, pages 3757-3762.
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HélioA. Stefani, JoãoV. Comasseto, Nicola Petragnani, AntonioL. Braga, PauloH. Menezes & ElenaV. Gusevskaya. (1997) NICKEL (II) CATALYZED SUBSTITUTION OF HALOGENS IN 1-HALO-1-CHALCOGENE ALKENES BY CHALCOGENATE ANIONS. Phosphorus, Sulfur, and Silicon and the Related Elements 126:1, pages 211-222.
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Yun Ma & Xian Huang. (1997) A Regiospecific Synthesis of 1-Iodo Arylselenoethenes via Hydrostannation of Arylselenoethynes. Synthetic Communications 27:2, pages 225-229.
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Xian Huang & Liu-Sheng Zhu. (1996) Stereoselective synthesis of (E)-Vinylic selenides. Synthetic Communications 26:4, pages 671-675.
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Articles from other publishers (40)

Francesca Begini, Renata A. Balaguez, Allya Larroza, Eric F. Lopes, Eder João Lenardão, Claudio Santi & Diego Alves. (2021) Synthesis of 4-Arylselanyl-1H-1,2,3-triazoles from Selenium-Containing Carbinols. Molecules 26:8, pages 2224.
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Dian-Liang Wang, Yi Fang, Shun-Yi Wang & Shun-Jun Ji. (2020) Silver-mediated activation of terminal alkynes: A strategy to construct bis-ethynynl selenides and tellurides. Tetrahedron 76:15, pages 131083.
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Khadijeh Didehban, Esmail Vessally, Akram Hosseinian, Ladan Edjlali & Ebrahim Saedi Khosroshahi. (2018) Nanocatalysts for C–Se cross-coupling reactions. RSC Advances 8:1, pages 291-301.
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Eric F. Lopes, Bianca T. Dalberto, Gelson Perin, Diego Alves, Thiago Barcellos & Eder J. Lenardão. (2017) Synthesis of Terminal Ethynyl Aryl Selenides and Sulfides Based on the Retro-Favorskii Reaction of Hydroxypropargyl Precursors. Chemistry - A European Journal 23:55, pages 13760-13765.
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Javier Peña, Garazi Talavera, Bernd Waldecker & Manuel Alcarazo. (2017) Alkynylthioimidazolium Salts: Efficient Reagents for the Synthesis of Alkynyl Sulfides by Electrophilic Thioalkynylation. Chemistry - A European Journal 23:1, pages 75-78.
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JOÃO V. Comasseto, Leandro Piovan & Edison P. Wendler. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups 1 78 .
Elmira Mohammadi & Barahman Movassagh. (2014) Cryptand-22 as an efficient ligand for the copper-catalyzed cross-coupling reaction of diorgano dichalcogenides with terminal alkynes leading to the synthesis of alkynyl chalcogenides. Tetrahedron Letters 55:9, pages 1613-1615.
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Dahan Eom, Sangjune Park, Youngchul Park, Kooyeon Lee, Gilbert Hong & Phil Ho Lee. (2013) Brønsted Acid Catalyzed Intramolecular Hydroarylation for the Synthesis of Cycloalkenyl Selenides and Tellurides. European Journal of Organic Chemistry 2013:13, pages 2672-2682.
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Syed M. Salman, Senthil Narayanaperumal, Ricardo S. Schwab, Caroline R. Bender, Oscar E. D. Rodrigues & Luciano Dornelles. (2012) CuO nano particles and [bmim]BF4: an application towards the synthesis of chiral β-seleno amino derivatives via ring opening reaction of aziridines with diorganyl diselenides. RSC Advances 2:22, pages 8478.
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Daniel S. Rampon, Rodrigo Giovenardi, Tiago L. Silva, Raoní S. Rambo, Aloir A. Merlo & Paulo H. Schneider. (2011) Chalcogenoacetylenes Obtained by Indium(III) Catalysis: Dual Catalytic Activation of Diorgano Dichalcogenides and Csp-H Bonds. European Journal of Organic Chemistry 2011:35, pages 7066-7070.
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João V. Comasseto, Alcindo A. Dos Santos & Edison P. Wendler. 2011. Organoselenium Chemistry. Organoselenium Chemistry 147 189 .
Paulo Henrique Menezes & Gilson Zeni. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups.
Nasir Baig Rashid Baig, R. N. Chandrakala, V. Sai Sudhir & Srinivasan Chandrasekaran. (2010) Synthesis of Unnatural Selenocystines and β-Aminodiselenides via Regioselective Ring-Opening of Sulfamidates Using a Sequential, One-Pot, Multistep Strategy. The Journal of Organic Chemistry 75:9, pages 2910-2921.
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Bin Huang, Shengyong You & Mingzhong Cai. (2010) Regio- and Stereoselective Synthesis of Tetrasubstituted Olefins by the Three-Component Tandem Reaction of Phenylselenomagnesium Bromide, Acetylenic Sulfones and Allylic Bromides. Journal of Chemical Research 34:3, pages 127-129.
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Antonio L. Braga, Ricardo S. Schwab, Eduardo E. Alberto, Syed M. Salman, Josimar Vargas & Juliano B. Azeredo. (2009) Ring opening of unprotected aziridines by zinc selenolates in a biphasic system. Tetrahedron Letters 50:20, pages 2309-2311.
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Gelson Perin, Eder João Lenardão, Raquel Guimarães Jacob & Rodrigo Barroso Panatieri. (2009) Synthesis of Vinyl Selenides. Chemical Reviews 109:3, pages 1277-1301.
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Antonio L. Braga, Fábio Z. Galetto, Paulo S. Taube, Márcio W. Paixão, Claudio C Silveira, Devender Singh & Fabrício Vargas. (2008) Mild and efficient one-pot synthesis of chiral β-chalcogen amides via 2-oxazoline ring-opening reaction mediated by indium metal. Journal of Organometallic Chemistry 693:24, pages 3563-3566.
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Anuj Sharma, Ricardo S. Schwab, Antonio L. Braga, Thiago Barcellos & Marcio W. Paixão. (2008) A convenient synthetic route for alkynylselenides from alkynyl bromides and diaryl diselenides employing copper(I)/imidazole as novel catalyst system. Tetrahedron Letters 49:35, pages 5172-5174.
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Nicola Petragnani & Hélio A. Stefani. (2005) Advances in organic tellurium chemistry. Tetrahedron 61:7, pages 1613-1679.
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Qing Xu & Xian Huang. (2004) cis -Carbocuperation of acetylenic sulfoxides and corresponding applications in the regio- and stereoselective synthesis of polysubstituted vinyl sulfoxides. Tetrahedron Letters 45:29, pages 5657-5660.
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Qing Xu, Xian Huang & Jun Ni. (2004) Hydrotelluration and carbotelluration of acetylenic sulfoxides: regio- and stereoselective preparation of α- and β-organotellurovinyl sulfoxides. Tetrahedron Letters 45:14, pages 2981-2984.
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Lothar W Bieber, Margarete F da Silva & Paulo H Menezes. (2004) Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes. Tetrahedron Letters 45:13, pages 2735-2737.
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Antonio L. Braga, Fabrı́cio Vargas, Gilson Zeni, Claudio C. Silveira & Leandro H. de Andrade. (2002) Synthesis of β-organotelluro vinylphosphine oxides by hydrotelluration of 1-alkynylphosphine oxides and their palladium-catalyzed cross-coupling with alkynes. Tetrahedron Letters 43:24, pages 4399-4402.
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Xian Huang & Meihua Xie. (2002) Stereoselective Michael−Aldol Tandem Reaction of Phenylselenomagnesium Bromide with Acetylenic Sulfones and Aldehydes. An Efficient Synthesis of Polyfunctionalized Allylic Alcohols. Organic Letters 4:8, pages 1331-1334.
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Claudio C. Silveira, Antonio L. Braga & Robson B. Guerra. (2002) Stereoselective synthesis of α-phenylchalcogeno-α,β-unsaturated esters. Tetrahedron Letters 43:18, pages 3395-3397.
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Mei Su, Wensheng Yu & Zhendong Jin. (2001) A stereoselective synthesis of α-halo vinyl sulfides and their applications in organic synthesis. Tetrahedron Letters 42:23, pages 3771-3774.
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Yun Ma & Changtao Qian. (2000) [2+2] Cycloaddition reactions of imines with alkynyl selenides catalyzed by scandium triflate. Tetrahedron Letters 41:6, pages 945-947.
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Miguel J. Dabdoub, Mauro L. Begnini, Palimécio G. Guerrero & Adriano C. M. Baroni. (1999) Hydrozirconation of Lithium Alkynylselenolate Anions. Generation and Reactions of α-Zirconated Vinyl Selenide Intermediates. The Journal of Organic Chemistry 65:1, pages 61-67.
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Sylvain Ponthieux & Claude Paulmier. 2000. Organoselenium Chemistry. Organoselenium Chemistry 113 142 .
Claudio C Silveira, Gelson Perin, Antonio L Braga, Miguel J Dabdoub & Raquel G Jacob. (1999) Synthesis of ketene (S, Te)acetals and their transformation into Z-α-phenylthio-α,β-unsaturated aldehydes. Tetrahedron 55:24, pages 7421-7432.
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Thomas G. Back, Richard J. Bethell, Masood Parvez & Daniel Wehrli. (1998) Additions of Organocopper Reagents and Heteroatom Nucleophiles to 1-Phenylseleno-2-( p -toluenesulfonyl)ethyne. Preparation of Vinyl and Allenic Sulfones and Formation of Michael, Anti-Michael, and Rearrangement Products . The Journal of Organic Chemistry 63:22, pages 7908-7919.
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Miguel J. Dabdoub, Mauro L. Begnini & Palimécio G. GuerreroJr.Jr.. (1998) Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates. Tetrahedron 54:11, pages 2371-2400.
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G. Pattenden, J. I. G. Cadogan & S. V. LeyG. Pattenden, J. I. G. Cadogan & S. V. Ley. 1997. Dictionary of Organic Compounds. Dictionary of Organic Compounds 199 216 .
Xian Huang & Liu-Sheng Zhu. (1996) Stereoselective synthesis of (E)-vinylic selenides by palladium catalyzed cross-coupling reactions. Journal of Organometallic Chemistry 523:1, pages 9-11.
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Liu-Sheng Zhu, Zhi-Zhen Huang & Xian Huang. (1996) Stereoselective synthesis of (E,E)-1-arylselenobutadienes by cross-coupling reactions in the presence of palladium catalyst. Tetrahedron 52:29, pages 9819-9822.
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João V. Comasseto, Paulo H. Menezes, Helio A. Stefani, Gilson Zeni & Antônio L. Braga. (1996) Addition of hydrogen halides to acetylenic selenides. Synthesis of 1-halo-1-selenoalkenes. Tetrahedron 52:29, pages 9687-9702.
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Miguel J. Dabdoub, Tânia M. Cassol & Sandro L. Barbosa. (1996) Synthesis of ketene butyltelluro(phenylseleno)acetals by the Al/Te exchange reaction. Tetrahedron Letters 37:6, pages 831-834.
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Claudio C. Silveira, Gelson Perin & Antonio L. Braga. (1995) Synthesis of ketene phenyltelluroacetals by a Wittig-Horner route. Tetrahedron Letters 36:41, pages 7361-7362.
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Marco Tingoli, Marcello Tiecco, Lorenzo Testaferri, Andrea Temperini, Giancarlo Pelizzi & Alessia Bacchi. (1995) Alkynyl phenyl selenides as convenient precursors for the synthesis of stereodefined trisubstituted alkenes. Tetrahedron 51:16, pages 4691-4700.
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A. L. BRAGA, A. RECKZIEGEL, C. C. SILVEIRA & J. V. COMASSETO. (2010) ChemInform Abstract: Vicinal Difunctionalization of Alkynyl Selenides (I) with Lithium Butylcyanocuprate and Electrophiles.. ChemInform 25:43.
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