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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 17
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Original Articles

Indium-Mediated Michael Addition of Allyl Bromide to 1,1-Dicyano-2-arylethenes in Aqueous Media

Lei Wang Department of Chemistry, Hangzhou University, Hangzhou, 310028, P. R. China
,
Xinghua Sun Department of Chemistry, Hangzhou University, Hangzhou, 310028, P. R. China
&
Yongmin Zhang Department of Chemistry, Hangzhou University, Hangzhou, 310028, P. R. China
Pages 3263-3267 | Received 11 Mar 1998, Published online: 23 Aug 2006

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WarjeetS. Laitonjam, Bhavna Thingom & SoniyaD. Moirangthem. (2013) Indium-mediated Michael Addition of Methyl (Z)-2-(Bromomethyl)-3-phenylacrylate to Arylidenemalononitriles in Aqueous Medium. Organic Preparations and Procedures International 45:3, pages 246-251.
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AndrÉAC. Galindo, JulianaM. Oliveira, MariaA. G. Barboza, SimoneM.C. Gonçalves & PauloH. Menezes. (2001) Synthesis of Chalcogenides using Indium Intermediates in Aqueous Media. Phosphorus, Sulfur, and Silicon and the Related Elements 172:1, pages 129-140.
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Articles from other publishers (34)

Michael Z. Liang & Simon J. Meek. (2020) Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones. Journal of the American Chemical Society 142:22, pages 9925-9931.
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Qiong Tang, Kai Fu, Peiran Ruan, Shunxi Dong, Zhishan Su, Xiaohua Liu & Xiaoming Feng. (2019) Asymmetric Catalytic Formal 1,4‐Allylation of β,γ‐Unsaturated α‐Ketoesters: Allylboration/Oxy‐Cope Rearrangement. Angewandte Chemie International Edition 58:34, pages 11846-11851.
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Qiong Tang, Kai Fu, Peiran Ruan, Shunxi Dong, Zhishan Su, Xiaohua Liu & Xiaoming Feng. (2019) Asymmetric Catalytic Formal 1,4‐Allylation of β,γ‐Unsaturated α‐Ketoesters: Allylboration/Oxy‐Cope Rearrangement. Angewandte Chemie 131:34, pages 11972-11977.
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Timothy B. Lowinger, Teck-Peng Loh, Michael R. Pitts, Angel Resendez, Chris L. Murphy & Rachel Snelling. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 22 .
Zhi-Liang Shen, Shun-Yi Wang, Yew-Keong Chok, Yun-He Xu & Teck-Peng Loh. (2012) Organoindium Reagents: The Preparation and Application in Organic Synthesis. Chemical Reviews 113:1, pages 271-401.
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Chao-Jun Li. (2011) Unorthodox chemistry for an unorthodox challenge: Exploration of new chemical reactivities for a sustainable future. Science China Chemistry 54:12, pages 1815-1830.
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Sung Hwan Kim, Hyun Seung Lee, Ko Hoon Kim, Se Hee Kim & Jae Nyoung Kim. (2010) Recent advances in allylindium reagents in organic synthesis. Tetrahedron 66:35, pages 7065-7076.
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Ujjal Kanti Roy & Sujit Roy. (2010) Making and Breaking of Sn−C and In−C Bonds in Situ: The Cases of Allyltins and Allylindiums. Chemical Reviews 110:4, pages 2472-2535.
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Joshua D. Waetzig, Elizabeth C. Swift & Elizabeth R. Jarvo. (2009) Conjugate allylation reactions of alkylidene malononitriles mediated by NHC-ligated palladium catalysts. Tetrahedron 65:16, pages 3197-3201.
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Laura A.T. Cleghorn, Ronald Grigg, Vladimir Savic & Milena Simic. (2008) Reactive organoallyl species generated from aryl halides and allene: allylation of α,β-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes. Tetrahedron 64:37, pages 8731-8737.
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Chao‐Jun Li. 2007. Organic Reactions in Water. Organic Reactions in Water 92 145 .
. (2007) Indium and Gallium-Mediated Addition Reactions. Bulletin of the Korean Chemical Society 28:1, pages 17-28.
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S. Araki & T. Hirashita. 2007. Comprehensive Organometallic Chemistry III. Comprehensive Organometallic Chemistry III 649 751 .
Chao-Jun Li. (2005) Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations:  A Decade Update. Chemical Reviews 105:8, pages 3095-3166.
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Virender, Suman L. Jain & Bir Sain. (2005) Indium-mediated, highly efficient cyclopropanation of olefins using CH2I2 as methylene transfer reagent. Tetrahedron Letters 46:1, pages 37-38.
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Phil Ho Lee, Sundae Kim, Kooyeon Lee, Dong Seomoon, Hyunseok Kim, Seokju Lee, Misook Kim, Mijeong Han, Kwanghyun Noh & Tom Livinghouse. (2004) Cyclization of 1-Bromo-2,7- and 1-Bromo-2,8-Enynes Mediated by Indium. Organic Letters 6:26, pages 4825-4828.
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. (2004) Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones. Bulletin of the Korean Chemical Society 25:11, pages 1687-1691.
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Brindaban C. Ranu & Arijit Das. (2004) Indium(I) iodide promoted highly selective 1,2-addition of allyl and benzyl groups to α,β-unsaturated nitriles under sonication: a new synthesis of conjugated imines. Tetrahedron Letters 45:37, pages 6875-6877.
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Min Wang, Lei Wang, Pin-Hua Li & Jin-Can Yan. (2010) A novel debromination of vic-dibromides to alkenes with InCl3(cat.)/Sm system in aqueous media. Chinese Journal of Chemistry 22:8, pages 863-866.
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Vijay Nair, Sindu Ros, C.N. Jayan & Bindu S. Pillai. (2004) Indium- and gallium-mediated carbon–carbon bond-forming reactions in organic synthesis. Tetrahedron 60:9, pages 1959-1982.
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Pinhua Li, Lei Wang, Yaner Yang, Xinhua Sun, Min Wang & Jincan Yan. (2004) A novel reduction of sodium alkyl thiosulfates with InCl 3 (cat.)/Sm(0) system in aqueous media: Facile synthesis of disulfides . Heteroatom Chemistry 15:5, pages 376-379.
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Kooyeon Lee, Hyunseok Kim, Tomoya Miura, Koichi Kiyota, Hiroyuki Kusama, Sunggak Kim, Nobuharu Iwasawa & Phil Ho Lee. (2003) Indium-Mediated β-Allylation, β-Propargylation, and β-Allenylation onto α,β-Unsaturated Ketones:  Reactions of in-Situ-Generated 3- tert -Butyldimethylsilyloxyalk-2-enylsulfonium Salts with in-Situ-Generated Organoindium Reagents . Journal of the American Chemical Society 125:32, pages 9682-9688.
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Phil Ho Lee, Dong Seomoon, Kooyeon Lee & Yunkiu Heo. (2003) Highly Efficient 1,4-Addition of 1,3-Diesters to Conjugated Enones by In/TMSCl. The Journal of Organic Chemistry 68:6, pages 2510-2513.
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Vijay Nair, C.N Jayan & Sindu Ros. (2001) Novel reactions of indium reagents with 1,2-diones: a facile synthesis of α-hydroxy ketones. Tetrahedron 57:46, pages 9453-9459.
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Phil Ho Lee, Kooyeon Lee & Sunggak Kim. (2001) A Novel Nucleophilic Substitution of in Situ Generated 3- tert -Butyldimethyl- silyloxyalk-2-enylsulfonium Salts with Allylindium Reagents . Organic Letters 3:20, pages 3205-3207.
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Phil Ho Lee, Hyosoon Ahn, Kooyeon Lee, Sun-young Sung & Sunggak Kim. (2001) Studies on the reactions of α,β-enones with allyl indium reagent; effects of TMSCl as promoter on regioselectivity. Tetrahedron Letters 42:1, pages 37-39.
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Soyeon Kang, Taeg-Su Jang, Gyochang Keum, Soon Bang Kang, So-Yeop Han & Youseung Kim. (2000) In/InCl 3 -Mediated Cross-Coupling Reactions of Methyl Vinyl Ketone with Benzaldehyde in Aqueous Media . Organic Letters 2:23, pages 3615-3617.
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Lothar W. Bieber, Rosenildo C. da Costa & Margarete F. da Silva. (2000) Reductive alkylation of nitrobenzene promoted by zinc and tin in protic solvents. Tetrahedron Letters 41:25, pages 4827-4830.
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J.S Yadav, B.V Subba Reddy & G.S Kiran Kumar Reddy. (2000) Indium-mediated allylation of gem-diacetates to homoallylic acetates in aqueous media. Tetrahedron Letters 41:15, pages 2695-2697.
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Vijay Nair & C.N Jayan. (2000) Indium mediated Barbier reactions of 1,2-diones: a facile synthesis of α-hydroxy ketones. Tetrahedron Letters 41:7, pages 1091-1094.
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Yang & Tak Hang Chan. (1999) Organic Reactions in Aqueous Media. Cyclopentadienylindium(I) as the First Example of Organoindium(I) Reagent for Carbon−Carbon Bond Formation and the Demonstration of One-Pot Tandem Addition/Intramolecular Diels−Alder Reaction in Aqueous Media. Journal of the American Chemical Society 122:2, pages 402-403.
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Chao-Jun Li & Tak-Hang Chan. (1999) Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 55:37, pages 11149-11176.
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Shuki Araki, Tomoaki Horie, Motoshi Kato, Tsunehisa Hirashita, Hatsuo Yamamura & Masao Kawai. (1999) Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents. Tetrahedron Letters 40:12, pages 2331-2334.
Crossref
L. WANG, X. SUN & Y. ZHANG. (2010) ChemInform Abstract: Indium‐Mediated Michael Addition of Allyl Bromide to 1,1‐Dicyano‐2‐arylethenes in Aqueous Media.. ChemInform 29:49.
Crossref

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