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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 11
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Original Articles

Selenium-Catalyzed Oxidative Carbonylation of Aniline and Alcohols to N-Phenylcarbamates

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Pages 1614-1624 | Received 02 Apr 2009, Published online: 06 May 2010

REFERENCES

  • Kim , H. S. ; Kim , Y. J. ; Lee , H. S. ; Lee , D. C. ; Chiny , S. Oxidative carbonylation of aromatic amines by selenium compounds . J. Catal. 1999 , 184 , 526 – 534 .
  • (a) Gupte , S. P. ; Shivarkar , A. B. ; Chaudhari , R. V. Carbamate synthesis by solid-base-catalyzed reaction of disubstituted ureas and carbonates . Chem. Commun. 2001 , 2620 – 2621 ; (b) Aresta , M. ; Quaranta , E. Carbon dioxide: A substitute for phosgene . Chem. Tech. 1997 , 27 , 32 – 40 ; (c) Vauthey , I. ; Valot , F. ; Gozzi , C. ; Fache , F. ; Lemane , M. An environmentally benign access to carbamates and ureas . Tetrahedron Lett. 2000 , 41 , 6347 – 6350 .
  • (a) Wu , T. T. ; Huang , J. ; Arrington , N. ; Dill , G. M. Synthesis and herbicidal activity of α-heterocyclic carbinol carbamates . J. Agric. Food Chem. 1987 , 35 , 817 – 823 ; (b) Dell'Amico , D. B. ; Calderazzo , F. ; Labella , L. ; Marchetti , F. ; Pampaloni , G. Converting carbon dioxide into carbamate derivatives . Chem. Rev. 2003 , 103 , 3857 – 3898 .
  • (a) Norwick , J. S. ; Powell , N. A. ; Nguyen , T. M. ; Noronha , G. An improved method for the synthesis of enantiomerically pure amino acid ester isocyanates . J. Org. Chem. 1992 , 57 , 7364 – 7366 ; (b) Tafesh , A. M. ; Weiguny , J. A review of the selective catalytic reduction of aromatic nitro compounds into aromatic amines, isocyanates, carbamates, and ureas using CO . Chem. Rev. 1996 , 96 , 2035 – 2052 .
  • (a) Uchiumi , P. S. ; Ataka , K. ; Matsuzaki , T. Oxidative reactions by a palladium–alkyl nitrite system . J. Organomet. Chem. 1999 , 576 , 279 – 289 ; (b) Majer , P. ; Randad , R. S. A safe and efficient method for preparation of N,N′-unsymmetrically disubstituted ureas utilizing triphosgene . J. Org. Chem. 1994 , 59 , 1937 – 1938 ; (c) Slocombe , R. J. ; Hardy , E. ; Saunders , J. H. ; Jenkins , R. L. Phosgene derivatives: The preparation of isocyanates, carbamyl chlorides, and cyanuric acid . J. Am. Chem. Soc. 1950 , 72 , 1888 – 1891 .
  • (a) Skoog , S. J. ; Campbell , J. P. ; Gladfelter , W. L. Homogeneous catalytic carbonylation of nitroaromatics, 9: Kinetics and mechanism of the first N-O bond cleavage and structure of the η-2-ArNO intermediate . Organometallics 1994 , 13 , 4137 – 4139 ; (b) Macho , V. ; Harustiak , M. New catalytic system for oxidative carbonylation of aniline . J. Mol. Catal. 1994 , 91 , L155 – L159 ; (c) Aresta , M. ; Quaranta , E. Alkali-metal-assisted transfer of the carbamate group from phosphocarbamates to alkyl halides: A new easy way to alkali-metal carbamates and to carbamate esters . J. Chem. Soc. Dalton Trans. 1992 , 1893 – 1899 .
  • Fukuoka , S. ; Chono , M. ; Kohno , M. A novel catalytic synthesis of carbamates by the oxidative alkoxycarbonylation of amines in the presence of platinum group metal and alkali metal halide or onium halide . J. Org. Chem. 1984 , 49 , 1458 – 1460 .
  • Ragaini , F. ; Cenini , S. Mechanistic studies of palladium-catalysed carbonylation reactions of nitro compounds to isocyanates, carbamates and ureas. J. Mol. Catal. A: Chem. 1996, 109, 1–25.
  • Curini , M. ; Epifano , F. ; Maltese , F. ; Rosati , O. Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis . Tetrahedron Lett. 2002 , 43 , 4895 – 4897 .
  • Salvatore , R. N. ; Shin , II , S. ; Nagle , A. S. ; Jumg , K. W. Efficient carbamate synthesis via a three-component coupling of an amine, CO2, and alkyl halides in the presence of Cs2CO3 and tetrabutylammonium iodide . J. Org. Chem. 2001 , 66 , 1035 – 1037 .
  • (a) Alper , H. ; Hartstock , F. W. An exceptionally mild, catalytic homogeneous method for the conversion of amines into carbamate esters . J. Chem. Soc. Chem. Commun. 1985 , 16 , 1141 – 1144 ; (b) Pisanu , T. ; Chuang , S. S. C. Carbamate synthesis on Pd/C catalysts: Gas−solid versus slurry processes . Ind. Eng. Chem. Res. 2004 , 43 , 1192 – 1199 .
  • (a) Li , K. T. ; Peng , Y. J. Oxidative carbonylation of aniline using manganese-based catalysts . J. Catal. 1993 , 143 , 631 – 634 ; (b) Gupte , S. P. ; Chaudhari , R. V. Oxidative carbonylation of aniline over Pd/C catalyst: Effect of promoters, solvents, and reaction conditions . J. Catal. 1988 , 114 , 246 – 258 .
  • Gupte , S. P. ; Chaudhari , R. V. Kinetic modeling of oxidative carbonylation of aniline over palladium/carbon-sodium iodide catalyst . Ind. Eng. Chem. Res. 1992 , 31 , 2069 – 2074 .
  • Giannoccaro , P. ; Nobile , C. F. ; Moro , G. Oxidative carbonylation of aniline catalyzed by Pd(II)-2,2′-bipyridyl complex intercalated in α-zirconium-phosphate . J. Mol. Catal. 1989 , 53 , 349 – 357 .
  • Wang , X. F. ; Lu , S. W. ; Yu , Z. K. Selenium-catalyzed carbonylation of nitroarenes to symmetrical 1,3-diarylureas under atmospheric pressure . Adv. Synth. Catal. 2004 , 346 , 929 – 932 .
  • Sonoda , N. ; Yasuhara , T. ; Kondo , K. ; Ikeda , T. ; Tsutsumi , S. New synthesis of ureas: Reaction of ammonia or aliphatic amines with carbon monoxide in the presence of selenium . J. Am. Chem. Soc. 1971 , 93 , 6344 .
  • Kondo , K. ; Sonoda , N. ; Sakurai , H. Selenium catalyzed synthesis of carbonates: The reaction of alkoxide with carbon monoxide and oxygen in the presence of selenium . Bull. Chem. Soc. Jpn. 1975 , 48 , 108 – 111 .
  • Kondo , K. ; Sonoda , N. ; Tsutsumi , S. A new synthesis of carbamates: The reaction of carbon monoxide with amine and alcohol in the co-presence of selenium and triethylamine . Chem. Lett. 1972 , 373 – 374 .
  • Sonoda , N. Selenium assisted carbonylation with carbon monoxide . Pure Appl. Chem. 1993 , 65 , 699 – 706 .
  • Sonoda , N. ; Yamamoto , G. ; Natsukawa , K. ; Kondo , K. ; Murai , S. A new synthesis of heterocycles by the reaction of amino alcohols or amino thiols with carbon monoxide in the presence of selenium . Tetrahedron Lett. 1975 , 16 , 1969 – 1972 .
  • Yang , Y. ; Lu , S. W. Selenium-catalyzed reductive carbonylation of PhNO2 in alcohol media to phenyl carbamates . Chin. J. Catal. 1999 , 20 , 224 – 226 .
  • George , D. K. ; Moore , D. H. ; Brian , W. P. ; Garman , J. A. Carbamate herbicides, relative herbicidal, and growth-modifying activity of several esters of N-phenylcarbamic acid . J. Agric. Food Chem. 1954 , 2 , 356 – 363 .
  • Whitmore , F. C. ; Popkin , A. H. ; Whitaker , J. S. ; Mattil , K. F. ; Zech , J. D. The action of primary Grignard reagents on t-butylacetyl chloride . J. Am. Chem. Soc. 1938 , 60 , 2462 – 2464 .
  • Schicktanz , S. T. ; Etienne , A. D. ; Steele , W. I. Analysis of fusel oil by azeotropic distillation . Ind. Eng. Chem. Anal. Ed. 1939 , 11 , 420 – 422 .
  • Herbert , E. ; Ungnade , D. V. N. The effect of bases on the hydrogenation of alkylphenols in the presence of Raney nickel. J. Am. Chem. Soc. 1944, 66, 1218–1220.
  • Dominguez , X. ; Lopez , I. ; Franc , R. Simple preparation of a very active Raney nickel catalyst . J. Org. Chem. 1961 , 26 , 1625 .
  • Dewey , B. T. ; Witt , N. F. Identification of alcohols . Ind. Eng. Chem. Anal. Ed. 1940 , 12 , 459 – 460 .

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