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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 6
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Original Articles

Raney Nickel–Catalyzed Hydrogenation of Unsaturated Carboxylic Acids with Sodium Borohydride in Water

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Pages 893-904 | Received 23 Jun 2010, Published online: 11 Nov 2011

REFERENCES

  • (a) Hudlicky , M. Reductions in Organic Chemistry ; John Wiley & Sons : New York , 1984 ; (b) Raylander , P. N. Hydrogenation Methods ; Academic Press : San Diego , 1994 ; (c) Kendall, J. K.; Fisher, T. H. An improved synthesis of 6,8-dimethoxy-3-methylisocoumarin, a fungal metabolite precursor. J. Org. Chem. 1989, 54, 4218–4220; (d) Woodword R. B.; Sondheimer, F.; Taub, D.; Heusler, K.; McLamore, W. M. The total synthesis of steroids. J. Am. Chem. Soc. 1952, 74, 4223–4251; (e) Larock, R. C. Comprehensive Organic Transformations–A Guide to Functional Group Transformations, 2nd ed.; Wiley-VCH: 1999.
  • Parshal , G. W. Catalysis in molten salt media. J. Am. Chem. Soc. 1972, 94, 8716–8719.
  • (a) Falk , G. C. Facile olefin hydrogenation with soluble lithiurn-based coordination catalysts . J. Org. Chem. 1971 , 36 , 1445 – 1446 ; (b) Stuermer , R. ; Hauer , B. ; Hall , M. ; Faber , K. Asymmetric bioreduction of activated C=C bonds using enoatereductase from the old yellow enzyme family . Curr. Opin. Chem. Bio. 2007 , 11 , 203 – 213 ; (c) Fryszkowska , A. ; Fischer , K. ; Gardiner , J. M. ; Stephens , G. M. Highly enantioselective reduction of, β,β-disubstituted aromatic nitro alkenes catalyzed by clostridium sporogenes . J. Org. Chem. 2008 , 73 , 4295 – 4298 ; (d) Hall , M. ; Stueckler , C. ; Kroutil , W. ; Macheroux , P. ; Faber , K. Asymmetric bioreduction of activated alkenes using cloned 12-oxophytodienoate reductase isoenzymes OPR-1 and OPR-3 from lycopersion esculentum(tomato): A striking change of stereoselectivity . Angew. Chem. Int. Ed. 2007 , 46 , 3934 – 3937 ; (e) Kosjek , B. ; Fleitz , F. J. ; Dormer , P. G. ; Kuethe , J. T. ; Devine , P. N. Asymmetric bioreduction of α,β-unsaturated nitriles and ketones . Tetrahedron: Asymmetry 2008 , 19 , 1403 – 1406 .
  • (a) Park , K. H. ; Rapoport , H. Enantioselective synthesis of (1R,4S)-l-amino-4-(hydroxymethyl)-2-cyclopentene, a precursor for carbocyclic nucleoside synthesis . J. Org. Chem. 1994 , 59 , 394 – 399 ; (b) Adams , R. ; Shriner , R. L. Platinum oxide as a catalyst in the reduction of organic compounds. III. Preparation and properties of the oxide of platinum obtained by the fusion of chloroplatinic acid with sodium nitrate . J. Am. Chem. Soc. 1923 , 45 , 2171 – 2179 .
  • (a) Brown , C. A. Catalytic hydrogenation, V: The reaction of sodium borohydride with aqueous nickel salts: P-1 nickel boride, a convenient, highly active nickel hydrogenation catalyst . J. Org. Chem. 1970 , 35 , 1900 – 1904 ; (b) Adkins , H. ; Cramer , H. I. The use of nickel as a catalyst for hydrogenation . J. Am. Chem. Soc. 1930 , 52 , 4349 – 4358 .
  • (a) Brown , H. C. ; Brown , C. A. A simple preparation of highly active platinum metal catalysts for catalytic hydrogenation . J. Am. Chem. Soc. 1962 , 84 , 1494 – 1495 ; (b) Brown , C. A. ; Ahuja , V. K. Catalytic hydrogenation, VI: The reaction of sodium borohydride with nickel salts in ethanol solution. P-2 nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure . J. Org. Chem. 1973 , 38 , 2226 – 2230 ; (c) Satoh , T. ; Mitsuo , N. ; Nishiki , M. ; Nanba , K. ; Suzuki , S. A new powerful and selective reducing agent sodium borohydride–palladium chloride system . Chem. Lett. 1981 , 1029 – 1030 ; (d) Yakabe , S. ; Hirano , M. ; Morimoto , T. Hydrogenation of alkenes with sodium borohydride and moist alumina catalyzed by nickel chloride . Tetrahedron Lett. 2000 , 41 , 6795 – 6798 ; (e) Ranu , B. C. ; Samanta , S. Reduction of activated conjugated alkenes by the InCl3–NaBH4 reagent system . Tetrahedron 2003 , 59 , 7901 – 7906 ; (f) Ranu , B. C. ; Samanta , S. Remarkably selective reduction of the α,β-carbon–carbon double bond in highly activated α,β,γ,δ-unsaturated alkenes by the InCl3-NaBH4 reagent system . J. Org. Chem. 2003 , 68 , 7130 – 7132 ; (g) Adair , G. R. A. ; Kapoor , K. K. ; Scolan , A. I. B. ; Williams , J. M. J. Ruthenium catalysed reduction of alkenes using sodium borohydride . Tetrahedron Lett. 2006 , 47 , 8943 – 8944 ; (h) Kalashnikov , V. V. ; Tomillova , I. G. Catalytic reduction of an α,β–disubstituted alkene with sodium borohydride in presence of tetra-tert-butylphthalocyanine complexes . Mendeleev Commun. 2007 , 17 , 343 – 344 ; (i) Aramini , A. ; Brinchi , L. ; Germani , R. ; Savelli , G. Reductions of α,β-unsaturated ketones by NaBH4 or NaBH4 + CoCl2: Selectivity control by water or by aqueous micellar solutions . Eur. J. Org. Chem. 2000 , 1793 – 1797 .
  • (a) Gribble , G. W. Sodium borohydride in carboxylic acid media: A phenomenal reduction system . Chem. Soc. Rev. 1998 , 27 , 395 – 404 ; (b) Chum , P. W. ; Wilson , S. E. Reduction of alkynes and monosubstituted alkenes with lithium aluminum hydride and titanium tetrachloride . Tetrahedron Lett. 1976 , 17 , 15 – 16 ; (c) Ashby , E. C. ; Lin , J. J. Reduction of alkenes, alkynes, and halides by lithium aluminum hydride–transition metal chloride . Tetrahedron Lett. 1977 , 18 , 4481 – 4484 ; (d) Ashby , E. C. ; Lin , J. J. Selective reduction of alkenes and alkynes by the reagent lithium aluminium hydride–transition-metal halide . J. Org. Chem. 1978 , 43 , 2567 – 2572 ; (e) Tour , J. M. ; Cooper , J. P. ; Pendalwar , S. L. Highly selective heterogeneous palladium-catalyzed hydrogenations using triethoxysilane and water . J. Org. Chem. 1990 , 55 , 3452 – 3453 ; (f) Tour , J. M. ; Pendalwar , S. L. Selective heterogeneous palladium-catalyzed hydrogenations of water-soluble alkenes and alkynes . Tetrahedron Lett. 1990 , 31 , 4719 – 4722 ; (g) Wang , J. ; Song , G. ; Peng , Y. ; Zhu , Y. 3-Butyl-1-methylimidazolinium borohydride ([bmim] [BH4])—A novel reducing agent for the selective reduction of carbon–carbon double bonds in activated conjugated alkenes . Tetrahedron Lett. 2008 , 49 , 6518 – 6520 ; (h) Mirza , A. M. ; Boukherroub , R. ; Bolourtchain , M. ; Hosseini , M. Palladium-catalyzed reduction of olefins with triethylsilane . Tetrahedron Lett. 2003 , 44 , 4579 – 4580 ; (i) Chamberlin , A. R. ; Dezube , M. ; Reich , S. H. ; Sall , D. J. Enantioselective total synthesis of 9s-dihydroerythronolide a seco acid . J. Am. Chem. Soc. 1989 , 111 , 6247 – 6256 .
  • Dondoni , A. ; Perrone , D. ; Semola , M. T. Thiazole-based stereoselective routes to leucine and phenylalanine hydroxyl ethylene dipeptide isostere inhibitors of renin and HIV-1 aspartic protease. J. Org. Chem. 1995, 60, 7927–7933.
  • Sharma , P. K. ; Kumar , S. ; Kumar , P. ; Nielson , P. Selective reduction of mono- and disubstituted olefins by NaBH4 and catalytic RuCl3 . Tetrahedron Lett. 2007 , 48 , 8704 – 8708 .
  • Tran , A. T. ; Huyanth , V. A. ; Friz , E. M. ; Whiteny , S. K. ; Cordes , D. B. A general method for the rapid reduction of alkenes and alkynes using sodium borohydride, acetic acid, and palladium . Tetrahedron Lett. 2009 , 50 , 1817 – 1819 .
  • (a) Varma , R. S. Solvent-free organic syntheses using supported reagents and microwave irradiation . Green Chem. 1999 , 1 , 43 – 45 ; (b) Loupy , A. ; Petit , A. ; Hamelin , J. ; Texier-Boullet , F. ; Jacqualt , P. ; Mathe , D. New solvent-free organic synthesis using focused microwave . Synthesis 1998 , 1213 – 1234 ; (c) Deshayes , S. ; Liagre , M. ; Loupy , A. ; Luche , J. L. ; Petit , A. Microwave activation in phase transfer catalysis . Tetrahedron 1999 , 55 , 10851 – 10870 ; (d) Kidwai , M. Dry media reactions . Pure Appl. Chem. 2001 , 73 , 147 – 151 ; (e) Narayan , S. ; Muldoon , J. ; Finn , M. G. ; Fokin , V. V. ; Kolb , H. C. ; Sharpless , K. B. “On water”: Reactivity of organic compounds in aqueous suspension . Angew. Chem. Int. Ed. 2005 , 44 , 3275 – 3279 ; (f) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
  • Mal , D. ; Majumdar , G. ; Pal , R. Stereospecfic formation of 2-[(E)-alk-1′-enyl]benzoic acids in an unusual reaction of thiophthalides with aldehydes . J. Chem. Soc., Perkin Trans. I 1994 , 1115 – 1116 .
  • (a) Kollonitsch , J. I. ; Mertel , H. E. ; Verdi , V. F. Preparation of ortho-alkyl- and ortho-aralkylbenzoic acids by catalytic hydrogenation of ortho-acylbenzoic acids . J. Org. Chem. 1962 , 27 , 3362 – 3363 ; (b) Albouy , D. ; Moghadam , G. E. ; Vinatoru , M. ; Koenig , M. Regenerative role of the red phosphorous in couple HIaeq/Pred . J. Orgmetallic. Chem. 1997 , 529 , 295 – 299 .
  • (a) Quinn , J. F. ; Razzano , D. A. ; Golden , K. C. ; Gregg , B. T. 1,4-Cyclohexadiene with Pd/C as a rapid, safe transfer hydrogenation system with microwave heating . Tetrahedron Lett. 2008 , 49 , 6137 – 6140 ; (b) Schweuk , E. ; Papa , D. Preparation of aryl aliphatic acids by the modified Willgerodt reaction . J. Org. Chem. 1946 , 11 , 798 – 802 ; (c) O'Connell , J. L. ; Simpson , J. S. ; Dumanski , P. G. ; Simpson , G. W. ; Easton , C. J. Aromatic chlorination of ω-phenyl alkyl amines and ω-phenyl alkyl amides in carbon tetrachloride and α,α,α-trifluorotoluene . Org. Biomol. Chem. 2006 , 4 , 2716 – 2723 .
  • (a) Haadsma-Svenson , S. R. ; Cleek , K. A. ; Dinh , D. M. ; Duncan , J. N. ; Haber , C. L. ; Huff , R. M. ; Lajiness , M. E. ; Nichols , N. F. ; Smith , M. W. ; Svenson , K. A. ; Zaya , M. J. ; Carlsson , A. ; Lin , C. H. Dopamine D3 receptor antagonists, 1: Synthesis and structure-activity relationships of 5,6-dimethoxy-N-alkyl- and N-alkylaryl-substituted 2-aminoindans. J. Med. Chem. 2001, 44, 4716–4732.
  • Friedman , B. S. ; Cotton , S. M. Hydrogen fluoride–catalyzed reactions of hydrocarbons with carbon monoxide . Angew. Chem. 1962 , 27 , 481 – 486 .
  • Kawashima , M. ; Sato , T. ; Fujisawa , T. A facile method for synthesis of three carbon-homologated carboxylic acid by regioselective ring-opening of β-propiolactones with organo copper reagents . Tetrahedron 1989 , 45 , 403 – 412 .
  • (a) Schelkun , R. M. ; Yuen , P. ; Wustrow , D. J. ; Kinsora , J. ; Zhisu , T. ; Vartanian , M. G. Heteroaromatic side-chain analogs of pregabalin . Bioorg. Med. Chem. Lett. 2006 , 16 , 2329 – 2332 ; (b) Scrapa , J. S. ; Ribi , M. ; Eugster , C. H. Zur Kenntnis des Fuerstions: Synthesen alkylsubstituierter phtalshuren . Helv. Chim. Acta 1966 , 49 , 858 – 870 .
  • Amsberry , K. L. ; Borchardt , R. T. The lactonization of 2′-hydroxyhydrocinnamic acid amides: A potential prodrug for amines . J. Org. Chem. 1990 , 55 , 5867 – 5877 .
  • Balasubramaniyan , V. ; Bhattia , V. G. ; Wagh , S. B. Facile esterification of carboxylic acids with organophosrous reagents: Novel application of alkylphosphoric esters . Tetrahedron 1983 , 39 , 1475 – 1485 .
  • Hamon , D. P. G. ; Massy-Westropp , R. A. ; Newton , J. L. Enantioselective syntheses of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs and related compounds . Tetrahedron 1995 , 51 , 12645 – 12650 .
  • Kabalka , G. W. ; Bierer , D. Trimethylsilyl esters: Protection of carboxylic acids during hydroboration reactions . Organometallics 1989 , 8 , 655 – 659 .
  • Pierce , J. S. ; Salsbury , J. M. ; Fredericksen , J. M. Local anesthetics, I: β-Monoalkyl aminoethyl esters of alkoxybenzoic acids . J. Am. Chem. Soc. 1942 , 64 , 1691 – 1694 .
  • Sakaguchi , H. Amides and method for plant control with the same. U.S. Patent 0122064 A1, 2006 .
  • Buchi , V. J. ; Laucner , H. ; Meyer , R. ; Lieberherr , R. Synthese und spasmolytische Wirkung einiger Esterather von disubstituierten Glykolsauren . Helv. Chim. Acta 1951 , 40 , 373 – 381 .
  • Alonso , F. ; Osante , I. ; Yus , M. Highly selective hydrogenation of multiple carbon–carbon bonds promoted by nickel(0) nanoparticles . Tetrahedron 2007 , 63 , 93 .

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