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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 16-17
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Original Articles

Chemoselective Reductions with Sodium Borohydride. Aldehydes vs. Ketones

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Pages 1927-1933 | Published online: 05 Dec 2006

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Read on this site (6)

Sosale Chandrasekhar & Annadka Shrinidhi. (2014) Selective Aldehyde Reduction in Ketoaldehydes with NaBH4-Na2CO3-H2O at Room Temperatures. Synthetic Communications 44:14, pages 2051-2056.
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Kiyoshi Tanemura, Tsuneo Suzuki, Yoko Nishida, Koko Satsumabayashi & Takaaki Horaguchi. (2005) Chemoselective Reduction of Aldehydes in the Presence of Ketones with NaBH4 in Polyethylene Glycol Dimethyl Ethers. Synthetic Communications 35:6, pages 867-872.
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DaleE. Ward & Yuanzhu Gai. (1997) Simple Methods for the Preparation of Enantiomerically Pure Abscisic Acid (ABA) Analogues from (S)-(+)-ABA. Synthetic Communications 27:12, pages 2133-2142.
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Liu Fu-Chu, Li Wan-Xun, Wang You-Chu & Lin Jun. (1995) Convenient Syntheses of Some Analogs of the Sex Pheromone of Citrus Mealybug, Planococcus citri (Risso). Synthetic Communications 25:23, pages 3837-3843.
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Articles from other publishers (35)

Narges Seyedi, Leyla Nazemi‐Nasyrmahale, Farhad Shirini & Hassan Tajik. (2023) Highly Selective Reduction of Carbonyl Compounds and O ‐Acetylation of Arylalcohols in the Presence of a Nickel Ion‐Containing 1,4‐Diazabicyclo[2.2.2]octane (DABCO)‐Based Ionic Liquid . ChemistrySelect 8:5.
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Nibin K. Mathew, Rohith Vinod K, Theertharaman G, M. Navaneethan & S. Balakumar. (2023) Probing the influence of liquid nitrogen assisted chemical reduction on the nature of passivation layer, magnetic properties, and Cr (VI) remediation performance of nanoscale zero valent iron. Journal of Environmental Chemical Engineering 11:1, pages 109096.
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Luke R. Churchman, Lauren J. Salisbury & James J. De Voss. (2022) Synthesis of obtusifoliol and analogues as CYP51 substrates. Organic & Biomolecular Chemistry 20:36, pages 7316-7324.
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Mohammed Gamal, Hazim M. Ali, Rania El-Shaheny, Ibrahim A. Naguib, Izzeddin Alsalahat & Mahmoud El-Maghrabey. (2022) Facile Conversion of the Quinone-Semicarbazone Chromophore of Naftazone into a Fluorescent Quinol-Semicarbazide: Kinetic Study and Analysis of Naftazone in Pharmaceuticals and Human Serum. Sensors 22:16, pages 6205.
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Rohmad Yudi Utomo, Febri Wulandari, Dhania Novitasari, Beni Lestari, Ratna Asmah Susidarti, Riris Istighfari Jenie, Jun-ya KatoSardjiman Sardjiman & Edy Meiyanto. (2021) Preparation and Cytotoxic Evaluation of PGV-1 Derivative, CCA-1.1, as a New Curcumin Analog with Improved-Physicochemical and Pharmacological Properties. Advanced Pharmaceutical Bulletin 12:3, pages 603-612.
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Guoqing Sui, Qingyun Lv, Xiaoqing Song, Huihui Guo, Jiatong Dai, Li Ren, Chi-Sing Lee, Wenming Zhou & Hong-Dong Hao. (2019) Chemoselective reduction of aldehydes via a combination of NaBH 4 and acetylacetone . New Journal of Chemistry 43:39, pages 15793-15796.
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Joo Yeon Kim, Won Kyu Shin, Ashok Kumar Jaladi & Duk Keun An. (2018) Chemoselective reduction of aldehydes and ketones by potassium diisobutyl-t-butoxy aluminum hydride (PDBBA). Tetrahedron 74:31, pages 4236-4241.
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Richard C. LarockRichard C. Larock & Cristiano Raminelli. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 69 .
Sireesha Malladi, R. Venkata Nadh, K. Suresh Babu & P. Suri Babu. (2017) Synthesis and antibacterial activity studies of 2,4-di substituted furan derivatives. Beni-Suef University Journal of Basic and Applied Sciences 6:4, pages 345-353.
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Ji Yeon Park, Won Kyu Shin, Ashok Kumar Jaladi & Duk Keun An. (2016) Reactions of a novel modified Red-Al reducing agent with selected organic compounds containing representative functional groups and chemoselective reduction. Tetrahedron Letters 57:30, pages 3247-3251.
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T. Ghosh, T. Slanina & B. König. (2015) Visible light photocatalytic reduction of aldehydes by Rh( iii )–H: a detailed mechanistic study . Chemical Science 6:3, pages 2027-2034.
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Davood Setamdideh, Zahra Karimi & Avat Alipouramjad. (2013) NaBH 4 /DOWEX(R)50WX4: A Convenient Reducing System for Fast and Efficient Reduction of Carbonyl Compounds to Their Corresponding Alcohols . Journal of the Chinese Chemical Society 60:6, pages 590-596.
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Moslem M. Lakouraj, Mahmood Tajbakhsh & Majid S. Mahalli. (2007) Ionene-Bound Borohydrides: Efficient, Selective, and Versatile Polymer-Supported Reducing Agents. Monatshefte für Chemie - Chemical Monthly 139:2, pages 117-123.
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Hossein MAHDAVI & Ekram HAGHANI. (2008) Poly(diallyldimethylammonium chloride) as an Efficient Phase Transfer Catalyst in Solvent‐Free Reduction of Carbonyl Compounds with NaBH 4 . Chinese Journal of Chemistry 26:2, pages 333-337.
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H. Mahdavi, E. Haghani & B. Malakian. (2006) Cross-linked poly(diallyldimethylammonium chloride) as an efficient solid–liquid phase transfer catalyst in reduction of carbonyl compounds with sodium borohydride. Reactive and Functional Polymers 66:10, pages 1033-1040.
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Behzad Zeynizadeh & Tarifeh Behyar. (2005) Wet THF as a Suitable Solvent for a Mild and Convenient Reduction of Carbonyl Compounds with NaBH 4 . Bulletin of the Chemical Society of Japan 78:2, pages 307-315.
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. (2003) (Pyridine)(tetrahydroborato)zinc Complex, [Zn(BH 4 ) 2 (py)], as a New Stable, Efficient and Chemoselective Reducing Agent for Reduction of Carbonyl Compounds . Bulletin of the Korean Chemical Society 24:4, pages 453-459.
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Yan Xing Jia, Xin Li, Bin Wu, Xue Zhi Zhao & Yong Qiang Tu. (2002) A convergent synthesis of the spiroketal moiety of the HIV-1 protease inhibitors didemnaketals. Tetrahedron 58:9, pages 1697-1708.
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Qin Caiqin, Xiao Ling, Du Yumin, Shi Xiaowen & Chen Jiawei. (2002) A new cross-linked quaternized-chitosan resin as the support of borohydride reducing agent. Reactive and Functional Polymers 50:2, pages 165-171.
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Hong Zhu, Tomoo Mizugaki, Kohki Ebitani & Kiyotomi Kaneda. (2001) Dimethylaminoethylated hydroxypropyl-chitosan: Preparation and application as polymeric ligand to form Rh6 cluster complexes for the reduction of benzaldehyde and nitrobenzene. Journal of Applied Polymer Science 80:3, pages 447-453.
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Zhanru Yu, Sonia Alesso, David Pears*Paul A Worthington, Richard W.A Luke & Mark Bradley. (2000) Acetoacetoxy ethyl methacrylate (AAEM) resin, a new scavenger for primary amines in the presence of secondary amines. Tetrahedron Letters 41:46, pages 8963-8967.
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Bernhard Kammermeier. 2000. Ullmann's Encyclopedia of Industrial Chemistry. Ullmann's Encyclopedia of Industrial Chemistry.
Ewa Krawczyk & Aleksandra Skowro?ska. (2000) A novel one-pot synthetic method for ?-methylenation of lactones and cycloalkanones based on thiophosphates. Heteroatom Chemistry 11:5, pages 353-361.
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Peter G. Goekjian, Priscilla Lugo-Mas, Stacy L. Cable, John O. Cole, James W. White, Dale J. Thompson, Tamara P. Dudley, Michael R. Jirousek, Jeffrey T. Dixon & Lawrence M. Ballas. (1999) Synthesis of indole-ring fluorine-labeled analogs of LY333531, an isoform-selective inhibitor of protein kinase C. Journal of Fluorine Chemistry 98:2, pages 137-142.
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Peter G. Goekjian, Guo-Zhang Wu, Shi Chen, Lanxin Zhou, Michael R. Jirousek, James R. Gillig, Lawrence M. Ballas & Jeffrey T. Dixon. (1999) Synthesis of Fluorinated Macrocyclic Bis(indolyl)maleimides as Potential 19 F NMR Probes for Protein Kinase C . The Journal of Organic Chemistry 64:12, pages 4238-4246.
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Tomoo Mizugaki, Kohki Ebitani & Kiyotomi Kaneda*. (1997) Highly Chemoselective Reduction of Aldehyde Function Catalyzed by Polymer-Bound Rh6 Cluster Complex under Water-Gas Shift Reaction Conditions. Tetrahedron Letters 38:17, pages 3005-3008.
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Béatrice David & Francis Schuber. (1996) Synthesis of α-difluoro and α-difluoro-β-trifluoroketo-derivatives as potential inhibitors for Cholesterol Ester Hydrolase. Bioorganic & Medicinal Chemistry Letters 6:14, pages 1673-1676.
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Habib Firouzabadi & Gholam Reza Afsharifar. (1995) Modified Borohydride Agents, 1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane Tetrahydroborate (BAAOTB) versus Tetrabutylammonium Tetrahydroborate (TBATB). Efficient, Selective, and Versatile Reducing Agents. Bulletin of the Chemical Society of Japan 68:9, pages 2595-2602.
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Kevin E.B. Parkes & Stewart K. Richardson. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 111 204 .
E. M. Groen‐Piotrowska & M. B. Groen. (2010) Total synthesis of (+)‐13‐ethyl‐3‐methoxygona‐1,3,5,9(11)‐tetraen‐17‐one via the tandem Claisen‐ene strategy. Recueil des Travaux Chimiques des Pays-Bas 112:12, pages 627-634.
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Nicholas Greeves. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 1 24 .
Wolfgang Giersch & Karl H. Schulte‐Elte. (2004) Enantiomeric 3,7‐Dimethylocta‐1,7‐dienes as Useful Chiral Building Blocks. A New Access to Both Optical Antipodes of Natural ( E )‐3,7‐Dimethyloct‐2‐ene‐1,8‐diol and ( E )‐3,7‐Dimethyloct‐2‐ene‐1,8‐dicarboxylic Acid . Helvetica Chimica Acta 73:3, pages 733-738.
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Brindaban C. Ranu & Rupak Chakraborty. (1990) Chemoselective reduction of aldehydes with zinc borohydride in tetrahydrofuran. Tetrahedron Letters 31:52, pages 7663-7664.
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D. E. WARD & C. K. RHEE. (1989) ChemInform Abstract: Chemoselective Reductions with Sodium Borohydride. Aldehydes vs. Ketones.. ChemInform 20:17.
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