Mild and Efficient PtO₂-Catalyzed One-Pot Reductive Mono-N-alkylation of Nitroarenes

REFERENCES

• (a) Gordon , E. M. ; Barret , R. W. ; Dower , W. J. ; Fodor , S. P. A. ; Gallop , M. A. Applications of combinatorial technologies to drug discovery, 1: Background and peptide combinatorial libraries . J. Med. Chem. 1994 , 37 , 1385 ; (b) Merla , B. ; Risch , N. Efficient synthesis of diastereomerically pure 1,3-diamines . Synthesis 2002 , 1365 ; (c) Henkel , T. ; Brunne , R. M. ; Mueller , H. ; Reichel , F. Statistical investigation into the structural complementarity of natural products and synthetic compounds . Angew. Chem. Int. Ed. 1999 , 38 , 643 .
   PubMed Web of Science ®Google Scholar
• Sharp , D. B. Metolachlor . In Herbicides: Chemistry, Degradation, and Mode of Action ; P. C. Kearney , D. D. Kaufman (Eds.); Marcel Dekker : New York , 1988 ; Chapter 7.
   Google Scholar
• Larock , R. C. Comprehensive Organic Transformations, , 2nd ed. ; Wiley-VCH : New York , 1999 ; p. 789 .
   Google Scholar
• Larock , R. C. Comprehensive Organic Transformations, , 2nd ed. ; Wiley-VCH : New York , 1999 ; p. 835 .
   Google Scholar
• (a) Lingaiah , N. ; Babu , N. S. ; Reddy , K. M. ; Prasad , P. S. S. ; Suryanarayana , I. An efficient reusable silver-exchanged tungstophosphoric acid heterogeneous catalyst for solvent-free intermolecular hydroamination of alkynes . Chem. Commun. 2007 , 278 ; (b) Komeyama , K. ; Morimoto , T. ; Takaki , K. A simple and efficient iron-catalyzed intramolecular hydroamination of unactivated olefins . Angew. Chem. Int. Ed. 2006 , 45 , 2938 .
   Web of Science ®Google Scholar
• Hutchins , R. O. ; Natale , N. R. Cyanoborohydride: Utility and applications in organic synthesis . Org. Prep. Proced. Int. 1979 , 11 , 201 .
   Web of Science ®Google Scholar
• Borch , R. F. ; Bernstien , M. D. ; Durst , H. D. Cyanohydridoborate anion as a selective reducing agent . J. Am. Chem. Soc. 1971 , 93 , 2897 .
   Web of Science ®Google Scholar
• Abdel-Magid , A. F. ; Carson , K. G. ; Harris , B. D. ; Maryanoff , C. A. ; Shah , R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride: Studies on direct and indirect reductive amination procedures . J. Org. Chem. 1996 , 61 , 3849 .
   PubMed Web of Science ®Google Scholar
• (a) Bomann , M. D. ; Guch , I. C. ; DiMare , M. J. A mild, pyridine-borane-based reductive amination protocol . J. Org. Chem. 1995 , 60 , 5995 ; (b) Pelter , A. ; Rosser , R. M. ; Mills , S. Reductive aminations of ketones and aldehydes using borane–pyridine . J. Chem. Soc., Perkin Trans. 1 1984 , 717 ; (c) Moorman , A. E. Reductive amination of piperidines with aldehydes using borane-pyridine . Synth. Commun. 1993 , 23 , 789 .
   Web of Science ®Google Scholar
• Tarasevich , V. A. ; Kozlov , N. G. Reductive amination of oxygen-containing organic compounds . Russ. Chem. Rev. 1999 , 68 , 55 .
   Google Scholar
• Micovic , I. V. ; Ivanovic , M. D. ; Piatak , D. M. ; Bojic , V. D. A simple method for preparation of secondary aromatic amines . Synthesis 1991 , 1043 .
   Web of Science ®Google Scholar
• Chen , B.-C. ; Sundeen , J. E. ; Guo , P. ; Bednarz , M. S. ; Znao , R. Novel triethylsilane-mediated reductive N-alkylation of amines: Improved synthesis of 1-(4-imidazolyl) methyl-4-sulfonylbenzodiazepines, new farnesyltransferase inhibitors . Tetrahedron Lett. 2001 , 42 , 1245 .
   Web of Science ®Google Scholar
• Suwa , T. ; Sugiyama , E. ; Shibata , I. ; Baba , A. Chemoselective reductive amination of aldehydes and ketones by dibutylchlorotin hydride–HMPA complex . Synthesis 2000 , 6 , 789 .
   Google Scholar
• Lee , O. Y. ; Law , K. L. ; Ho , C. ; Yang , Y. D. Highly chemoselective reductive amination of carbonyl compounds promoted by InCl3/Et3SiH/MeOH system . J. Org. Chem. 2008 , 73 , 8829 .
   PubMed Web of Science ®Google Scholar
• Gnanamgari , D. ; Moores , A. ; Rajaseelan , E. ; Crabtree , R. H. Transfer hydrogenation of imines and alkenes and direct reductive amination of aldehydes catalyzed by triazolederived iridium(I) carbene complexes . Organometallics 2007 , 26 , 1226 .
   Web of Science ®Google Scholar
• Imao , D. ; Fujihara , S. ; Yamamoto , T. ; Ohta , T. ; Ito , Y. Effective reductive amination of carbonyl compounds with hydrogen catalyzed by iridium complex in organic solvent and in ionic liquid . Tetrahedron 2005 , 61 , 6988 .
   Web of Science ®Google Scholar
• Tararov , V. I. ; Kadyrov , R. ; Riermeierc , T. H. ; Borner , A. On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(I) complexes. Chem. Commun. 2000, 1867.
   Web of Science ®Google Scholar
• (a) Lane , C. F. Sodium Cyanoborohydride—A highly selective reducing agent for organic functional groups . Synthesis 1975 , 135 ; (b) Bhattacharyya , S. Reductive amination with zinc borohydride: Efficient, safe route to fluorinated benzylamines . Synth. Commun. 1997 , 4265 ; (e) Ranu , B. C. ; Majee , A. ; Sarkar , A. One-pot reductive amination of conjugated aldehydes and ketones with silica gel and zinc borohydride . J. Org. Chem. 1998 , 63 , 370 ; (f) Bhattacharyya , S. ; Neidigh , K. A. ; Avery , M. A. ; Williamson , J. C. Selective monoalkylation of ammonia: A high-throughput synthesis of primary amines . Synlett 1999 , 1781 ; (g) Saxena , I. ; Borah , R. ; Sarma , J. C. Reductive amination of aromatic aldehydes and ketones with nickel boride . J. Chem. Soc., Perkin Trans. 1 2000 , 503 .
   Google Scholar
• (a) Bhanushali , M. J. ; Nandurkar , N. S. ; Bhor , M. D. ; Bhanage , B. M. Direct reductive amination of carbonyl compounds using bis(triphenylphosphine) copper(I) tetrahydroborate . Tetrahedron Lett. 2007 , 48 , 1273 ; (b) Robichaud , A. ; Ajjou , A. N. First example of direct reductive amination of aldehydes with primary and secondary amines catalyzed by water-soluble transition-metal catalysts . Tetrahedron Lett. 2006 , 47 , 3633 ; (c) Sato , S. ; Sakamoto , T. ; Miyazawa , E. ; Kikugawa , Y. One-pot reductive amination of aldehydes and ketones with α-picoline-borane in methanol, in water, and in neat conditions . Tetrahedron 2004 , 60 , 7899 .
   Web of Science ®Google Scholar
• Bae , J. W. ; Cho , Y. J. ; Lee , S. H. ; Yoon , C. O. M. ; Yoon , C. M. A one-pot synthesis of N-alkylaminobenzenes from nitroaromatics: Reduction followed by reductive amination using B10H14 . Chem. Commun. 2000 , 1857 .
   Web of Science ®Google Scholar
• Byun , E. ; Hong , B. ; De Castro , K. A. ; Lim , M. ; Rhee , H. One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes . J. Org. Chem. 2007 , 72 , 9815 .
   PubMed Web of Science ®Google Scholar
• Sydnes , M. O. ; Kuse , M. ; Isobe , M. Reductive monoalkylation of nitro aryls in one pot . Tetrahedron 2008 , 64 , 6406 .
   Web of Science ®Google Scholar
• Sreedhar , B. ; Reddy , P. S. ; Devi , D. K. Direct one-pot reductive amination of aldehydes with nitroarenes in a domino fashion: Catalysis by gum-acacia-stabilized palladium nanoparticles . J. Org. Chem. 2009 , 74 , 8806 .
   PubMed Web of Science ®Google Scholar
• Sreedhar , B. ; Reddy , P. S. ; Reddy , M. A. ; Neelima , B. ; Arundhathi , R. AgOTf-catalyzed direct amination of benzyl alcohols with sulphonamides . Tetrahedron Lett. 2007 , 46 , 8174 .
   Web of Science ®Google Scholar
• Hudlicky , M. Reductions in Organic Chemistry ; John Wiley and Sons : New York , 1984 ; p. 11 .
   Google Scholar
• March , J. Advanced Organic Chemistry, , 4th ed. ; John Wiley and Sons : New York , 1992 ; p. 881 .
   Google Scholar
• Hudlicky , M. Reductions in Organic Chemistry ; John Wiley and Sons : New York , 1984 ; p. 53 .
   Google Scholar
• Takasaki , M. ; Motoyama , Y. ; Higashi , K. ; Yoon , S. H. ; Mochida , I. ; Nagashima , H. Chemoselective hydrogenation of nitroarenes with carbon nanofiber-supported platinum and palladium nanoparticles . Org. Lett. 2008 , 10 , 1601 .
   PubMed Web of Science ®Google Scholar
• (a) Cho , B. T. ; Kang , S. K. Direct and indirect reductive amination of aldehydes and ketones with solid acid–activated sodium borohydride under solvent-free conditions . Tetrahedron 2005 , 61 , 5725 – 5734 ; (b) Liao , W. ; Chen , Y. ; Liu , Y. ; Duan , H.; Petersena, J. L. ; Shi , X. 1,2,3-Triazole-boranes: Stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water . Chem. Commun. 2009 , 6436 – 6438 ; (c) He , R. ; Toy , P. H. ; Lama , Y. Polymer-supported hantzsch 1,4-dihydropyridine ester: An efficient biomimetic hydrogen source . Adv. Synth. Catal. 2008 , 350 , 54 – 60 .
   Web of Science ®Google Scholar
• (a) Zhang , H. ; Cai , Q. ; Ma , D. Amino acid–promoted cui-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles. J. Org. Chem. 2005, 70, 5164–5173; (b) Yang , C. T. ; Fu , Y. ; Huang , Y. B. ; Yi , J. ; Guo , Q. X. ; Liu , L. Room-temperature copper-catalyzed carbon–nitrogen coupling of aryl iodides and bromides promoted by organic ionic bases. Angew. Chem. Int. Ed. 2009, 48, 7398–7401.
   PubMed Web of Science ®Google Scholar
• Ulgen , M. ; Gorrod , J. W. Microsomal formation of N-benzyl-4-hydroxymethylaniline from N-benzyl-4-methylaniline . J. Pharm. Pharmacol . 1992 , 865 – 866 .
   PubMed Web of Science ®Google Scholar
• (a) Zhu , X. ; Su , L. ; Huang , L. ; Chen , G. ; Wang , J. ; Song , H. ; Wan , Y. A facile and efficient oxalyldihydrazide/ketone-promoted copper-catalyzed amination of aryl halides in water . Eur. J. Org. Chem. 2009 , 635 – 642 .
   Web of Science ®Google Scholar