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Pure Appl. Chem., 1993, Vol. 65, No. 4, pp. 699-706

http://dx.doi.org/10.1351/pac199365040699

Selenium assisted carbonylation with carbon monoxide

N. Sonoda

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  • Tian Fengshou, Chen Yahong, Li Peng, Lu Shiwei: A Convenient Method to Synthesize 1,3-Selenazolidin-2-ones from 2-Chloroethyl Amine Salts by Se/CO System under Atmospheric Pressure and Temperature. Heteroatom Chem. 2013, 24, 524. <http://dx.doi.org/10.1002/hc.21127>
  • Sturgeon Ralph E., Grinberg Patricia: Some speculations on the mechanisms of photochemical vapor generation. J Anal Spectrom 2012, 27, 222. <http://dx.doi.org/10.1039/c2ja10249h>
  • SONODA N.: ChemInform Abstract: Selenium Assisted Carbonylation with Carbon Monoxide. ChemInform 2010, 24, no. <http://dx.doi.org/10.1002/chin.199326291>
  • Mizuno Takumi, Nakai Takeo, Mihara Masatoshi: Facile synthesis of glycerol carbonate from glycerol using selenium-catalyzed carbonylation with carbon monoxide. Heteroatom Chem 2010, 21, 541. <http://dx.doi.org/10.1002/hc.20640>
  • Wu Xiaowei, Yu Zhengkun: Metal and phosgene-free synthesis of 1H-quinazoline-2,4-diones by selenium-catalyzed carbonylation of o-nitrobenzamides. Tetrahetron Lett 2010, 51, 1500. <http://dx.doi.org/10.1016/j.tetlet.2010.01.040>
  • Zhang Xiaopeng, Jing Huanzhi, Zhang Guisheng: Selenium-Catalyzed Oxidative Carbonylation of Aniline and Alcohols to N-Phenylcarbamates. Synth Comm 2010, 40, 1614. <http://dx.doi.org/10.1080/00397910903134626>
  • Han Hoon, Chang Suk-Bok: Metal-Free Conversion of Carboxamides to Ureas Using Tertiary Amines and Iodosylmesitylene. Bulletin of the Korean Chemical Society 2010, 31, 746. <http://dx.doi.org/10.5012/bkcs.2010.31.03.746>
  • Zhang Xiaopeng, Jing Huanzhi: A facile one-pot phosgene-free synthesis of naphthalen-1-ylcarbamates by selenium-catalyzed carbonylation of 1-nitronaphthalene with carbon monoxide. Journal of Molecular Catalysis A 2009, 302, 137. <http://dx.doi.org/10.1016/j.molcata.2008.12.012>
  • Shelton Phillip A., Zhang Yue, Nguyen Thi Hoang Ha, McElwee-White Lisa: NaIO4-oxidized carbonylation of amines to ureas. Chem Commun 2009, 947. <http://dx.doi.org/10.1039/b819891h>
  • Chaturvedi Devdutt, Mishra Nisha, Mishra Virendra: A High Yielding, One-pot Synthesis of Substituted Ureas from the Corresponding Amines Using Mitsunobu’s Reagent. Monatshefte für Chemie 2008, 139, 267. <http://dx.doi.org/10.1007/s00706-007-0776-1>
  • Sommen Geoffroy L., Linden Anthony, Heimgartner Heinz: Selenium-Containing Heterocycles from Isoselenocyanates: Synthesis of 1,3-Selenazinane and 1,3-Selenazinanone Derivatives. HCA 2007, 90, 472. <http://dx.doi.org/10.1002/hlca.200790051>
  • Sommen Geoffroy L., Linden Anthony, Heimgartner Heinz: Selenium-Containing Heterocycles from Isoselenocyanates: Synthesis of 5-Amino-2,4-dihydro-3H-1,2,4-triazole-3-selones. HCA 2007, 90, 641. <http://dx.doi.org/10.1002/hlca.200790067>
  • Li Peng, Yuan Xiaohua, Wang Shudong, Lu Shiwei: A novel way to chiral 2-oxazolidinones: selenium-catalyzed cyclocarbonylation of 2-aminoethanols. Tetrahedron 2007, 63, 12419. <http://dx.doi.org/10.1016/j.tet.2007.09.037>
  • Sommen Geoffroy L., Linden Anthony, Heimgartner Heinz: Selenium-containing heterocycles from isoselenocyanates: synthesis of 2-methylidene-1,3-selenazolidine derivatives. Tetrahedron 2006, 62, 3344. <http://dx.doi.org/10.1016/j.tet.2006.01.077>
  • Zhao Xiaodan, Yu Zhengkun, Zeng Fanlong, Chen Jinzhu, Wu Xiaowei, Wu Sizhong, Xiao Wen-Jing, Zheng Zhaoyan: Highly Efficient Route to Diselenides from the Reactions of Imines and Selenium in the Presence of Carbon Monoxide and Water. Adv Synth Catal 2005, 347, 877. <http://dx.doi.org/10.1002/adsc.200404380>
  • Perveen Shahnaz, Abdul Hai Syed M., Khan Rashid A., Khan Khalid Mohammed, Afza Nighat, Sarfaraz Tahira B.: Expeditious Method for Synthesis of Symmetrical 1,3‐Disubstituted Ureas and Thioureas. Synth Common 2005, 35, 1663. <http://dx.doi.org/10.1081/SCC-200061656>
  • Chen Jinzhu, Lu Shiwei: Synthesis of substituted pyridyl ureas by selenium dioxide-catalyzed carbonylation. CATAL A GENERAL 2004, 261, 199. <http://dx.doi.org/10.1016/j.apcata.2003.11.042>
  • Chen Jinzhu, Ling Gang, Lu Shiwei: Synthesis of new unsymmetric N,N′-dipyridylurea derivatives by selenium and selenium dioxide-catalyzed reductive carbonylation of substituted nitropyridines. Tetrahedron 2003, 59, 8251. <http://dx.doi.org/10.1016/j.tet.2003.08.035>
  • Ling Gang, Chen Jinzhu, Lu Shiwei: Selenium-catalyzed carbonylation of substituted nitrobenzenes with aminomethylpyrimidines as co-reagents to synthesize N-phenyl-N′-methylpyrimidylurea derivatives. Journal of Molecular Catalysis A 2003, 202, 23. <http://dx.doi.org/10.1016/S1381-1169(03)00188-2>
  • Shi Feng, Deng Youquan, SiMa Tianlong, Yang Hongzhou: A novel ZrO2–SO42− supported palladium catalyst for syntheses of disubstituted ureas from amines by oxidative carbonylation. Tetrahetron Lett 2001, 42, 2161. <http://dx.doi.org/10.1016/S0040-4039(01)00124-1>
  • Delledonne Daniele, Rivetti Franco, Romano Ugo: Developments in the production and application of dimethylcarbonate. CATAL A GENERAL 2001, 221, 241. <http://dx.doi.org/10.1016/S0926-860X(01)00796-7>
  • Yang Hongzhou, Deng Youquan, Shi Feng: Synthesis of dialkylureas by electrocatalytical carbonylation of aliphatic amines under mild conditions. Journal of Molecular Catalysis A 2001, 176, 73. <http://dx.doi.org/10.1016/S1381-1169(01)00250-3>
  • McCusker Jennifer E., Qian Fang, McElwee-White Lisa: Catalytic oxidative carbonylation of aliphatic secondary amines to tetrasubstituted ureas. Journal of Molecular Catalysis A 2000, 159, 11. <http://dx.doi.org/10.1016/S1381-1169(00)00164-3>
  • Yang Ying, Lu Shiwei: Selenium-catalyzed reductive carbonylation of nitrobenzene with amines as coreagents to give unsymmetric phenylureas. Tetrahetron Lett 1999, 40, 4845. <http://dx.doi.org/10.1016/S0040-4039(99)00890-4>
  • Nishiyama Yutaka, Maema Ryo, Ohno Kengou, Hirose Masaharu, Sonoda Noboru: Synthesis of indoles: selenium-catalyzed reductive N-heterocyclization of 2-nitrostyrenes with carbon monoxide. Tetrahetron Lett 1999, 40, 5717. <http://dx.doi.org/10.1016/S0040-4039(99)01080-1>
  • Ryu Iihyong, Sonoda Noboru: Radikalische Carbonylierungen – gestern und heute. Angew Chem 1996, 108, 1140. <http://dx.doi.org/10.1002/ange.19961081005>
  • Ferraz de Souza Wladmir, Kambe Nobuaki, Sonoda Noboru: Theoretical study on structures and internal rotations of methylN,N-dimethylcarbamate and its sulphur, selenium, and tellurium homologues (Me2NC(O)YMe, Y = O,S,Se, Te). J Phys Org Chem 1996, 9, 179. <http://dx.doi.org/10.1002/(SICI)1099-1395(199603)9:3<179::AID-POC768>3.0.CO;2-L>
  • Macho Vendelín, Králik Milan, Halmo František: New catalytic system of N,N′-diphenylurea synthesis from nitrobenzene, carbon monoxide and water or aniline. Journal of Molecular Catalysis A 1996, 109, 119. <http://dx.doi.org/10.1016/1381-1169(96)00006-4>
  • Souza Wladmir Ferraz de, Kambe Nobuaki, Sonoda Noboru: A Theoretical Study on the Generation Process of Carbonyl Selenide in Selenium Catalyzed Carbonylation of Amines. Chem Lett 1996, 155. <http://dx.doi.org/10.1246/cl.1996.155>
  • Kato Shinzi, Kawachi Toshiaki, Ibi Kazumasa, Nakaiida Shoho, Kawai Kohji, Kanda Takahiro, Murai Toshiaki, Ishihara Hideharu: Synthesis and reaction of selenocarbamic acid sodium and potassium salts and organo-germanium, -tin, and -lead esters. Heteroatom Chem 1995, 6, 215. <http://dx.doi.org/10.1002/hc.520060306>
  • Besenyei Gábor, Németh Sándor, Simándi László I.: Carbonylation of selenilimines to arylsulfonyl isocyanates. Tetrahetron Lett 1994, 35, 9609. <http://dx.doi.org/10.1016/0040-4039(94)88523-0>
  • Tsunoi Shinji, Miyoshi Noritaka, Ogawa Akiya, Kambe Nobuaki, Sonoda Noboru: Purification of CO Based on Selenium-Amine-CO Chemistry. Bull Chem Soc Jpn 1994, 67, 2297. <http://dx.doi.org/10.1246/bcsj.67.2297>