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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 7
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Original Articles

Regiospecific Synthesis of Unsymmetrical α-Bromoketones

Robert E. Boyd R. W. Johnson Pharmaceutical Research Institute Welsh & McKean Roads, Spring House, Pennsylvania, 19477-0776
,
C. Royce Rasmussen R. W. Johnson Pharmaceutical Research Institute Welsh & McKean Roads, Spring House, Pennsylvania, 19477-0776
&
Jeffery B. Press R. W. Johnson Pharmaceutical Research Institute Welsh & McKean Roads, Spring House, Pennsylvania, 19477-0776
Pages 1045-1051 | Received 08 Sep 1994, Published online: 23 Sep 2006

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Rathinavel Jagatheesan, Pugalenthi Ramesh & Subramaniyan Sambathkumar. (2019) Selective α-bromination of aryl carbonyl compounds: prospects and challenges. Synthetic Communications 49:23, pages 3265-3289.
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Ateeq Rahman & S.B. Jonnalagadda. (2012) Simple and Efficient System for the α-Bromination of a β-Ketoester by Using N-Bromosuccinimide in the Presence of Silica-Supported NaHCO3 as the Heterogeneous Catalyst: An Environmentally Benevolent Approach. Synthetic Communications 42:8, pages 1091-1100.
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B. Sreedhar, P. Surendra Reddy & M. Madhavi. (2007) Rapid and Catalyst‐Free α‐Halogenation of Ketones using N‐Halosuccinamides in DMSO. Synthetic Communications 37:23, pages 4149-4156.
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Zhiguo Wang, Guodong Yin, Aihua Chen, Shengli Hu & Anxin Wu. (2007) Efficient Selective Formation of C‐C Single Bonds and C˭C Double Bonds by NBS‐Promoted Oxidative Coupling of β‐Keto Esters. Synthetic Communications 37:24, pages 4399-4405.
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J. Košmrlj, M. Kočevar & S. Polanc. (1996) A New Convenient Bromination with KBrO3/KBr/Dowex®. Synthetic Communications 26:19, pages 3583-3592.
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Articles from other publishers (26)

Dinesh Kumar Jangid & Surbhi Dhadda. 2020. Heterocycles - Synthesis and Biological Activities. Heterocycles - Synthesis and Biological Activities.
Zhiqi Lao, Huimiao Zhang & Patrick H. Toy. (2019) Reductive Halogenation Reactions: Selective Synthesis of Unsymmetrical α-Haloketones. Organic Letters 21:20, pages 8149-8152.
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Liang-Hua Zou, Yan-Chun Li, Ping-Gui Li, Jing Zhou & Zhimeng Wu. (2018) Solvent-Controlled α-Monobromination, α,α-Dibromination or Imidation of 1,3-Diketones with N -Bromosuccinimide . European Journal of Organic Chemistry 2018:41, pages 5639-5643.
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Richard C. LarockRichard C. Larock, Anton V. Dubrovskiy & Nataliya A. Markina. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 145 .
Richard C. LarockRichard C. Larock & Li Zhang. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 62 .
Juraj Velcicky, Wolfgang Miltz, Berndt Oberhauser, David Orain, Andrea Vaupel, Klaus Weigand, Janet Dawson King, Amanda Littlewood-Evans, Mark Nash, Roland Feifel & Pius Loetscher. (2017) Development of Selective, Orally Active GPR4 Antagonists with Modulatory Effects on Nociception, Inflammation, and Angiogenesis. Journal of Medicinal Chemistry 60:9, pages 3672-3683.
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Ranjana Aggarwal, Gulshan Singh, Dionisia Sanz, Rosa M. Claramunt, M. Carmen Torralba & M. Rosario Torres. (2016) NBS mediated one-pot regioselective synthesis of 2,3-disubstituted imidazo[1,2- a ]pyridines and their unambiguous characterization through 2D NMR and X-ray crystallography. Tetrahedron 72:27-28, pages 3832-3838.
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Indranirekha Saikia, Arun Jyoti Borah & Prodeep Phukan. (2016) Use of Bromine and Bromo-Organic Compounds in Organic Synthesis. Chemical Reviews 116:12, pages 6837-7042.
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Hossein Eshghi, Mehdi Bakavoli, Marjan Ghasemzadeh & Seyed Mohammad Seyedi. (2013) Ionic liquids bis(2-N-methylimidazoliumethyl)ether dichloroiodate/dibromochlorate as an efficient halogenating reagent for the synthesis of α-haloketones. Research on Chemical Intermediates 41:3, pages 1673-1682.
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Antonio Bermejo Gómez, Elis Erbing, María Batuecas, Ana Vázquez-Romero & Belén Martín-Matute. (2014) Iridium-Catalyzed Isomerization/Bromination of Allylic Alcohols: Synthesis of α-Bromocarbonyl Compounds. Chemistry - A European Journal 20:34, pages 10703-10709.
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Rajesh H. Vekariya & Hitesh D. Patel. (2014) Synthesis of α-bromocarbonyl compounds: recent advances. Tetrahedron 70:26, pages 3949-3961.
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Arun Kumar Macharla, Rohitha Chozhiyath Nappunni, Mahender Reddy Marri, Swamy Peraka & Narender Nama. (2012) Oxidative bromination of ketones using ammonium bromide and oxone®. Tetrahedron Letters 53:2, pages 191-195.
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Ye-Xiang Xie, Shi Tang, Qi-Ming Zhu, Du-Lin Yin & Jin-Heng Li. (2006) Selectiveα-Bromination ofβ-Keto Esters in Reusable PEG-400 under Mild and Catalyst-free Conditions. Chinese Journal of Chemistry 24:11, pages 1662-1664.
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Orazio A. Attanasi, Stefano Berretta, Gianfranco Favi, Paolino Filippone, Giuseppe Mele, Giada Moscatelli & Raffaele Saladino. (2006) Tetrabromo Hydrogenated Cardanol:  Efficient and Renewable Brominating Agent. Organic Letters 8:19, pages 4291-4293.
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Biswanath Das, Katta Venkateswarlu, Harish Holla & Maddeboina Krishnaiah. (2006) Sulfonic acid functionalized silica: A remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide. Journal of Molecular Catalysis A: Chemical 253:1-2, pages 107-111.
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H.M. Meshram, P.N. Reddy, P. Vishnu, K. Sadashiv & J.S. Yadav. (2006) A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids. Tetrahedron Letters 47:6, pages 991-995.
Crossref
Igor Pravst, Marko Zupan & Stojan Stavber. (2006) Solvent-free bromination of 1,3-diketones and β-keto esters with NBS. Green Chem. 8:11, pages 1001-1005.
Crossref
Kangying Li & Alexandre Alexakis. (2005) Copper catalyzed asymmetric conjugate addition-bromination of α,β-unsaturated ketones: a highly efficient one-pot reaction for the synthesis of chiral α-bromo-β-alkylketones. Tetrahedron Letters 46:35, pages 5823-5826.
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Matthew L. Meketa, Yogesh R. Mahajan & Steven M. Weinreb. (2005) An efficacious method for the halogenation of β-dicarbonyl compounds under mildly acidic conditions. Tetrahedron Letters 46:28, pages 4749-4751.
Crossref
Biswanath Das, Katta Venkateswarlu, Gurram Mahender & Ibram Mahender. (2005) A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst. Tetrahedron Letters 46:17, pages 3041-3044.
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H.M. Meshram, P.N. Reddy, K. Sadashiv & J.S. Yadav. (2005) Amberlyst-15®-promoted efficient 2-halogenation of 1,3-keto-esters and cyclic ketones using N-halosuccinimides. Tetrahedron Letters 46:4, pages 623-626.
Crossref
V. Caprio. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 135 214 .
Richard H. Blaauw, Jean-François Brière, Remco de Jong, Jorg C. J. Benningshof, Angeline E. van Ginkel, Jan Fraanje, Kees Goubitz, Henk Schenk, Floris P. J. T. Rutjes & Henk Hiemstra. (2000) Intramolecular Photochemical Dioxenone−Alkene [2 + 2] Cycloadditions as an Approach to the Bicyclo[2.1.1]hexane Moiety of Solanoeclepin A. The Journal of Organic Chemistry 66:1, pages 233-242.
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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 27 63 .
Bin Zheng & Morris Srebnik. (1995) A new directed synthesis of enol borates from gem-borazirconocene alkanes, and their regioselective conversion to α-bromo ketones. Tetrahedron Letters 36:32, pages 5665-5668.
Crossref
R. E. BOYD, C. R. RASMUSSEN & J. B. PRESS. (2010) ChemInform Abstract: Regiospecific Synthesis of Unsymmetrical α‐Bromoketones.. ChemInform 26:30.
Crossref

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