Transition Metal–Free Sodium Borohydride Promoted Controlled Hydration of Nitriles to Amides

REFERENCES

• (a) Zabicky , J. The Chemistry of Amides ; Wiley-Interscience : New York , 1970 ; (b) Greenberg , A. ; Breneman , C. M. ; Liebman , J. F. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science ; Wiley : New York , 2000 ; (c) Deopura , B. L. ; Gupta , B. ; Joshi , M. ; Alagirusami , R. Polyesters and Polyamides ; CRC Press : Boca Raton , FL , 2008 .
   Google Scholar
• (a) Opsahl , R. Encyclopedia of Chemical Technology ; Vol. 2 ; Wiley : New York , 1991 ; p. 346 ; (b) Ingvosersen , K. ; Kamphuis , J. Enzyme Catalysis in Organic Synthesis , Vol. 1 ; VCH : Weinheim , 1995 , pp. 365 – 392 .
   Google Scholar
• (a) Larock , R. C. Comprehensive Organic Transformations ; Wiley-VCH : New York , 1999; (b) Beckwith , A. L. J. In The Chemistry of Amides: Synthesis of Amides ; J. Zabicky (Ed.); Interscience : New York , 1970, p. 73; (c) Sydner , H. R. ; Elston , C. T. Polyphosphoric acid as a reagent in organic chemistry, VI: The hydrolysis of nitriles to amides. J. Am. Chem. Soc. 1954, 76, 3039–3040; (d) Hauser , C. R. ; Eby , C. J. The conversion of β-ketonitriles to β-ketoamides by boron fluoride in aqueous acetic acid and by polyphosphoric acid. J. Am. Chem. Soc. 1957, 79, 725–727; (e) McMaster , L. ; Langreck , F. B. The transformation of nitriles into amides by hydrogenperoxide. J. Am. Chem. Soc. 1917, 39, 103–109.
   Google Scholar
• (a) Mauger , J. ; Nagasawa , T. ; Yamada , H. Synthesis of various aromatic amide derivatives using nitrile hydratase of Rhodococcus rhodochrous J1 . Tetrahedron 1989 , 45 , 1347 – 1354 ; (b) Klempier , N. ; de Raadt , A. ; Faber , K. Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase . Tetrahedron Lett. 1991 , 32 , 341 – 344 ; (c) Kobayashi , M. ; Shimizu , S. Nitrile hydrolases . Curr. Opin. Chem. Biol. 2000 , 4 , 95 – 102 ; (d) Mylerova , V. ; Martinkova , L. Synthetic applications of nitrile converting enzymes . Curr. Org. Chem. 2003 , 7 , 1 – 17 ; (e) Kovacs , J. A. Synthetic analogues of cysteinate-ligated non-heme iron and non-corrinoid cobalt enzymes . Chem. Rev. 2004 , 104 , 825 – 848 .
   Web of Science ®Google Scholar
• Kukushkin , V. Y. ; Pombeiro , A. J. L. Metal-mediated and metal-catalyzed hydrolysis of nitriles . Inorg. Chim. Acta 2005 , 358 , 1 – 21 .
   Web of Science ®Google Scholar
• (a) Crestani , M. G. ; Arevalo , A. ; Garcia , J. J. Catalytic hydration of benzonitrile and acetonitrile using nickel(0) . Adv. Synth. Catal. 2006 , 348 , 732 – 742 ; (b) Crestani , M. G. ; Garcia , J. J. Catalytic hydration of mono and dinitriles using nickel(0) and PTSA . J. Mol. Catal. A: Chem. 2009 , 299 , 26 – 36 .
   Web of Science ®Google Scholar
• (a) Ghaffar , T. ; Parkins , A. W. The catalytic hydration of nitriles to amides using a homogeneous platinum phosphinito catalyst . J. Mol. Catal. A: Chem. 2000 , 160 , 249 – 261 ; (b) Jiang , X. ; Minnaard , A. J. ; Feringa , B. L. ; de Vries , J. G. Platinum-catalyzed selective hydration of hindered nitriles and nitriles with acid- or base-sensitive groups . J. Org. Chem. 2004 , 69 , 2327 – 2331 .
   Web of Science ®Google Scholar
• (a) Koffi-Bie Djoman , M. C. ; Ajjou , A. N. The hydration of nitriles catalyzed by water-soluble rhodium complexes . Tetrahedron Lett. 2000 , 41 , 4845 – 4849 ; (b) Goto , A. ; Endo , K. ; Saito , S. RhI-catalyzed hydration of organonitriles under ambient conditions . Angew. Chem. Int. Ed. 2008 , 47 , 3607 – 3609 .
   Web of Science ®Google Scholar
• (a) Tellers , D. M. ; Ritter , J. C. M. ; Bergman , R. G. Synthesis of iridium(III) carboxamides via the nimetallic reaction between Cp*(PMe3)IrPh(OH) and [Cp*(PMe3)Ir(Ph)NCR]+ . Inorg. Chem. 1999 , 38 , 4810 – 4818 ; (b) Chin , C. S. ; Chong , D. ; Lee , S. ; Park , Y. J. Addition of OH− and alcohols or amines to –C≡N and -CH˭CH2 groups of CH2 = CHCN coordinated to Cp*Ir(η 3-CH2CHCHPh) . Organometallics 2000 , 19 , 4043 – 4050 .
   PubMed Web of Science ®Google Scholar
• Breno , K. L. ; Pluth , M. D. ; Tyler , D. R. Organometallic chemistry in aqueous solution: Hydration of nitriles to amides catalyzed by a water-soluble molybdocene, (MeCp)2Mo(OH)(H2O)+ . Organometallics 2003 , 22 , 1203 – 1211 .
   Web of Science ®Google Scholar
• Ramon , R. S. ; Marion , N. ; Nolan , S. P. Gold activation of nitriles: Catalytic hydration to amides . Chem. Eur. J. 2009 , 15 , 8695 – 8697 .
   PubMed Web of Science ®Google Scholar
• (a) Breslow , R. ; Fairweather , R. ; Keana , J. Metal-catalyzed hydration of phenanthroline nitrile . J. Am. Chem. Soc. 1967 , 89 , 2135 – 2138 ; (b) Breslow , R. ; Schmir , M. Strongly catalyzed ligand–ligand reaction within a mixed metal complex . J. Am. Chem. Soc. 1971 , 93 , 4960 – 4961 .
   Web of Science ®Google Scholar
• (a) Clark , C. R. ; Hay , R. W. Reactions of co-ordinated nitriles, part II: Nickel(II)- and cobalt(II)-promoted hydrolysis of 2-cyano-8-hydroxyquinoline. Dalton Trans. 1974, 2148–2152; (b) Kim , J. H. ; Britten , J. ; Chin , J. Kinetics and mechanism of a cobalt(III) complex catalyzed hydration of nitriles. J. Am. Chem. Soc. 1993, 115, 3618–3622; (c) Chin , J. ; Kim , J. H. Catalytic hydration of acrylonitrile to acrylamide under mild conditions. Angew. Chem., Int. Ed. Engl. 1990, 29, 523–525; (d) Buckingham , D. A. ; Keene , F. R. ; Sargeson , A. M. Base hydrolysis of coordinated acetonitrile. J. Am. Chem. Soc. 1973, 95, 5649–5652.
   Web of Science ®Google Scholar
• (a) Paraskewas , S. Synthese von carbonsäureamiden durch partielle hydrolyse von PdCI2-nitril-komplexen . Synthesis 1974 , 574 ; (b) Ruiz , J. ; Cutillas , N. ; Rodriguez , V. ; Sampedro , J. ; Lopez , G. ; Chaloner , P. A. ; Hitchcock , P. Reactivity of hydroxo complexes of palladium(II) towards nitriles: Formation of carboxamide and imino ether derivatives of palladium(II) . Dalton Trans. 1999 , 2939 – 2946 .
   Google Scholar
• (a) Murahashi , S. I. ; Sasao , S. ; Satio , E. ; Naota , T. Ruthenium-catalyzed hydration of nitriles and transformation of δ-keto nitriles to ene-lactams . J. Org. Chem. 1992 , 57 , 2521 – 2523 ; (b) Cadierno , V. ; Francos , J. ; Gimeno , J. Selective ruthenium-catalyzed hydration of nitriles to amides in pure aqueous medium under neutral conditions . Chem. Eur. J. 2008 , 14 , 6601 – 6605 ; (c) Cavarzan , A. ; Scarso , A. ; Strukul , G. Efficient nitrile hydration mediated by Ru-II catalysts in micellar media . Green Chem. 2010 , 12 , 790 – 794 ; (d) Alvarez , R. G. ; Diez , J. ; Crochet , P. ; Cadierno , V. Arene-ruthenium(II) complexes containing amino-phosphine ligands as catalysts for nitrile hydration reactions . Organometallics 2010 , 29 , 3955 – 3965 ; (e) Yamaguchi , K. ; Matsushita , M. ; Mizuno , N. Efficient hydration of nitriles to amides in water, catalyzed by ruthenium hydroxide supported on alumina . Angew. Chem. 2004 , 116 , 1602 – 1606 .
   Web of Science ®Google Scholar
• Nolan , K. B. ; Hay , R. W. Reactions of co-ordinated nitriles, Part I: Reactions of cis-(aminoacetonitrile)bis(ethylenediamine)halogenocobalt(III) complexes in aqueous solution . Dalton Trans. 1974 , 914 – 920 .
   Web of Science ®Google Scholar
• Tamura , M. ; Wakasugi , H. ; Shimizu , K. ; Satsuma , A. Efficient and substrate-specific hydration of nitriles to amides in water by using a CeO2 catalyst . Chem. Eur. J. 2011 , 17 , 11428 – 11431 .
   PubMed Web of Science ®Google Scholar
• Moorthy , J. N. ; Singhal , N. Facile and highly selective conversion of nitriles to amides via indirect acid-catalyzed hydration using TFA or AcOH-H2SO4 . J. Org. Chem. 2005 , 70 , 1926 – 1929 .
   PubMed Web of Science ®Google Scholar
• (a) Sharma , U. ; Kumar , N. ; Verma , P. K. ; Kumar , V. ; Singh , B. Zinc phthalocyanine with PEG-400 as a recyclable catalytic system for selective reduction of aromatic nitro compounds . Green Chem. 2012 , 14 , 2289 – 2293 ; (b) Verma , P. K. ; Sharma , U. ; Kumar , N. ; Bala , M. ; Kumar , V. ; Singh , B. Nickel phthalocyanine–assisted highly efficient and selective carbonyl reduction in polyethylene glycol-400 . Catal. Lett. 2012 , 142 , 907 – 913 ; (c) Kumar , V. ; Sharma , U. ; Verma , P. K. ; Kumar , N. ; Singh , B. Cobalt(II) phthalocyanine-catalyzed highly chemoselective reductive amination of carbonyl compounds in a green solvent . Adv. Synth. Catal. 2012 , 354 , 870 – 878 ; (d) Sharma , U. ; Verma , P. K. ; Kumar , N. ; Kumar , V. ; Bala , M. ; Singh , B. Phosphane-free green protocol for selective nitro reduction with an iron-based catalyst . Chem. Eur. J. 2011 , 17 , 5903 – 5907 ; (e) Sharma , U. ; Verma , P. ; Kumar , N. ; Kumar , N. ; Singh , B. Highly chemo- and regioselective reduction of aromatic nitro compounds catalyzed by recyclable copper(II) as well as cobalt(II) phthalocyanines . Adv. Synth. Catal. 2010 , 352 , 1834 – 1840 .
   Web of Science ®Google Scholar
• Tao , T. ; Zhixun , W. ; Zelong , L. ; Xike , F. ; Qingyi , W. Efficient and practical transition metal-free catalytic hydration of organonitriles to amides . Green Chem. 2012 , 14 , 921 – 924 .
   Web of Science ®Google Scholar
• IHBT Communication No. 2369.
   Google Scholar