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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 2
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Original Articles

Palladium Catalyzed Allylation of Indole

W. E. Billups Department of Chemistry, Rice University Houston, Texas, 77031
,
Rodney S. Erkes Department of Chemistry, Rice University Houston, Texas, 77031
&
Larry E. Reed Department of Chemistry, Rice University Houston, Texas, 77031
Pages 147-154 | Received 31 Aug 1979, Published online: 05 Dec 2006

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Zhe Liu, Dong Wang, Yanchao Wu & Yongjun Chen. (2012) Mild and Efficient Allylation of Indoles and Amides Using Amberlyst-15 as a Recyclable Heterogeneous Catalyst. Synthetic Communications 42:12, pages 1813-1823.
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Articles from other publishers (51)

Mahesh H. Shinde & Chepuri V. Ramana. (2020) An Apparent Umpolung Reactivity of Indole through [Au]‐Catalysed Cyclisation and Lewis‐Acid‐Mediated Allylation. Chemistry – A European Journal 26:71, pages 17171-17175.
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Tamie Suzuki & John D. Chisholm. (2019) Friedel-Crafts alkylation of indoles with trichloroacetimidates. Tetrahedron Letters 60:19, pages 1325-1329.
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Barry M. Trost, Wen-Ju Bai, Christoph Hohn, Yu Bai & James J. Cregg. (2018) Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Substituted 1 H -Indoles and Tryptophan Derivatives with Vinylcyclopropanes . Journal of the American Chemical Society 140:21, pages 6710-6717.
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Ju Young Lee, Hyeri Ha, Seri Bae, Inhyuk Han & Jung Min Joo. (2016) Catalytic C-2 Allylation of Indoles by Electronic Modulation of the Indole Ring and its Application to the Synthesis of Functionalized Carbazoles. Advanced Synthesis & Catalysis 358:21, pages 3458-3470.
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Tetsuhiro Nemoto & Yasumasa Hamada. 2016. Asymmetric Dearomatization Reactions. Asymmetric Dearomatization Reactions 207 227 .
S. Senthilkumar & M. Kumarraja. (2015) Regioselective N-allylation and N-cinnamylation of indoles using CuI-exchanged hierarchical nanoporous material. Catalysis Communications 70, pages 86-89.
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Xiaojin Wu, Chuanhu Lei, Guizhou Yue & Jianrong (Steve) Zhou. (2015) Palladium‐Catalyzed Direct Cyclopropylation of Heterocycles. Angewandte Chemie International Edition 54:33, pages 9601-9605.
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Xiaojin Wu, Chuanhu Lei, Guizhou Yue & Jianrong (Steve) Zhou. (2015) Palladium‐Catalyzed Direct Cyclopropylation of Heterocycles. Angewandte Chemie 127:33, pages 9737-9741.
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Antoinette E. Nibbs, Thomas D. Montgomery, Ye Zhu & Viresh H. Rawal. (2015) Access to Spirocyclized Oxindoles and Indolenines via Palladium-Catalyzed Cascade Reactions of Propargyl Carbonates with 2-Oxotryptamines and Tryptamines. The Journal of Organic Chemistry 80:10, pages 4928-4941.
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Persis Dhankher, Laure Benhamou & Tom D. Sheppard. (2014) Rapid Assembly of Functionalised Spirocyclic Indolines by Palladium‐Catalysed Dearomatising Diallylation of Indoles with Allyl Acetate. Chemistry – A European Journal 20:41, pages 13375-13381.
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Thomas D. Montgomery, Antoinette E. Nibbs, Ye Zhu & Viresh H. Rawal. (2014) Rapid Access to Spirocyclized Indolenines via Palladium-Catalyzed Cascade Reactions of Tryptamine Derivatives and Propargyl Carbonate. Organic Letters 16:13, pages 3480-3483.
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Debjit Das & Sujit Roy. (2013) Palladium(II)‐Catalyzed Efficient C‐3 Functionalization of Indoles with Benzylic and Allylic Alcohols under Co‐Catalyst, Acid, Base, Additive and External Ligand‐Free Conditions. Advanced Synthesis & Catalysis 355:7, pages 1308-1314.
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Thomas D. Montgomery, Ye Zhu, Natsuko Kagawa & Viresh H. Rawal. (2013) Palladium-Catalyzed Decarboxylative Allylation and Benzylation of N -Alloc and N -Cbz Indoles . Organic Letters 15:5, pages 1140-1143.
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Jun Chen & Matthew J. Cook. (2013) Palladium Catalyzed Decarboxylative Rearrangement of N -Alloc Indoles . Organic Letters 15:5, pages 1088-1091.
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Feng-Quan Yuan, Feng-Yi Sun & Fu-She Han. (2012) A simple and efficient method for the allylation of heteroarenes catalyzed by PdCl2. Tetrahedron 68:34, pages 6837-6842.
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Sandro CacchiGiancarlo Fabrizi. (2011) Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions. Chemical Reviews 111:5, pages PR215-PR283.
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Jean Le Bras & Jacques Muzart. (2011) Intermolecular Dehydrogenative Heck Reactions. Chemical Reviews 111:3, pages 1170-1214.
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Feng-Quan Yuan, Lian-Xun Gao & Fu-She Han. (2011) PdCl2-catalyzed efficient allylation and benzylation of heteroarenes under ligand, base/acid, and additive-free conditions. Chemical Communications 47:18, pages 5289.
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Jie Jack Li & Gordon W. Gribble. 2010. Heterocyclic Scaffolds II:. Heterocyclic Scaffolds II: 193 234 .
Marco Bandini & Astrid Eichholzer. (2009) Catalytic Functionalization of Indoles in a New Dimension. Angewandte Chemie International Edition 48:51, pages 9608-9644.
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Marco Bandini & Astrid Eichholzer. (2009) Katalytische Funktionalisierung von Indolen in einer neuen Dimension. Angewandte Chemie 121:51, pages 9786-9824.
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Marco Bandini & Achille Umani‐Ronchi. 2009. Catalytic Asymmetric Friedel–Crafts Alkylations. Catalytic Asymmetric Friedel–Crafts Alkylations 145 166 .
Natsuko Kagawa, Jeremiah P. Malerich & Viresh H. Rawal. (2008) Palladium-Catalyzed β-Allylation of 2,3-Disubstituted Indoles. Organic Letters 10:12, pages 2381-2384.
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Gordon W. Gribble. 2007. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist 81 188 .
Shengming Ma, Shichao Yu, Zhihua Peng & Hao Guo. (2006) Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted Electron-Deficient Alkenes. The Journal of Organic Chemistry 71:26, pages 9865-9868.
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Mukund G. Kulkarni, Saryu I. Davawala, Attrimuni P. Dhondge, Dnyaneshwar D. Gaikwad, Ajit S. Borhade & Sanjay W. Chavhan. (2006) An efficient two-step synthesis of 3-allylindoles. Tetrahedron Letters 47:6, pages 1003-1005.
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Sandro Cacchi & Giancarlo Fabrizi. (2005) Synthesis and Functionalization of Indoles Through Palladium-catalyzed Reactions. Chemical Reviews 105:7, pages 2873-2920.
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Masanari Kimura, Makoto Futamata, Ryutaro Mukai & Yoshinao Tamaru. (2005) Pd-Catalyzed C3-Selective Allylation of Indoles with Allyl Alcohols Promoted by Triethylborane. Journal of the American Chemical Society 127:13, pages 4592-4593.
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Shengming Ma & Shichao Yu. (2004) Palladium-catalyzed functionalization of indoles with 2-acetoxymethyl substituted electron-deficient alkenes. Tetrahedron Letters 45:45, pages 8419-8422.
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Marco Bandini, Alfonso Melloni & Achille Umani-Ronchi. (2004) New Versatile Pd-Catalyzed Alkylation of Indoles via Nucleophilic Allylic Substitution:  Controlling the Regioselectivity. Organic Letters 6:18, pages 3199-3202.
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Vicenç Branchadell, Marcial Moreno-Mañas & Roser Pleixats. (2002) Theoretical Study on the Regioselectivity of Nucleophilic Attack in Silyl-Substituted (Diphosphino)(η 3 -allyl)palladium Cations . Organometallics 21:12, pages 2407-2412.
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Didier Stien, Glen T. Anderson, Charles E. Chase, Yung-hyo Koh & Steven M. Weinreb. (1999) Total Synthesis of the Antitumor Marine Sponge Alkaloid Agelastatin A. Journal of the American Chemical Society 121:41, pages 9574-9579.
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Glen T. Anderson, Charles E. Chase, Yung-hyo Koh, Didier Stien, Steven M. Weinreb & Maoyu Shang. (1998) Studies on Total Synthesis of the Cytotoxic Marine Alkaloid Agelastatin A. The Journal of Organic Chemistry 63:22, pages 7594-7595.
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Nicolas Vicart, Jacques Goré & Bernard Cazes. (1998) Palladium-catalyzed substitution of acrolein acetals by β-dicarbonyl nucleophiles. Tetrahedron 54:37, pages 11063-11078.
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J.-L. Malleron, J.-C. Fiaud & J.-Y. Legros. 1997. Handbook of Palladium-Catalyzed Organic Reactions. Handbook of Palladium-Catalyzed Organic Reactions 147 170 .
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