环氧化合物羰基化反应研究新进展

催化学报 , 2012, (9): 1435-1447. doi: 10.3724/SP.J.1088.2012.20515

环氧化合物羰基化反应研究新进展

樊启佳 ^1, , 刘建华 ^2, , 陈静 ^3, , 夏春谷 ^4,

1.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002; 兰州大学化学化工学院,甘肃兰州730000

2.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002

3.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002

4.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002

关键词：环氧化合物 , 羰基化扩环 , 羰基化开环共聚 , 羰基化开环 , 反应机理

FAN Qijia ^1, , LIU Jianhua ^2, , CHEN Jing ^3, , XIA Chungu ^4,

1.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002; 兰州大学化学化工学院,甘肃兰州730000

2.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002

3.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002

4.中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室,甘肃兰州7300002

通过催化的方法在有机化合物分子中引入羰基和其它基团而成为含氧化合物的羰基化反应,具有“原子经济性”反应的高选择性和对环境的友好性,可充分利用资源和保护环境,符合绿色化学发展趋势等优点,备受学术界及工业界青睐.综述了近年来羰基钴金属化合物催化的环氧化合物和一氧化碳羰基化反应研究的新进展,涉及的反应类型主要包括羰基化扩环、羰基化开环共聚以及羰基化开环,讨论了不同类型反应的相关机理,并展望了该领域的研究前景.

参考文献

[1]	Sneeden R P A;Tkatchenko I;Villeurbanne C N R S;Wilkinson G,Stone F G A,Abel E W.Comprehensive Organometallic Chemistry[M].New York:pergaman Press,1982:1.
[2]	Roelen O .[P].DE 849548,1938.
[3]	Kollár L.Modern Carbonylation Methods[M].Weinheim:John Wiley & Sons Inc,2008:1.
[4]	刘建华,陈静,孙伟,夏春谷.若干羰基化反应研究新进展[J].催化学报,2010(01):1-11.
[5]	刘建华,陈静,夏春谷.羰基化反应新技术研究进展[J].石油化工,2010(11):1189-1197.
[6]	Lu X B;Darensbourg D J .[J].Chemical Society Reviews,2012,41:1462.
[7]	Klaus S;Lehenmeier M W;Anderson C E;Rieger B .[J].Coordination Chemistry Reviews,2011,255:1460.
[8]	North M;Pasquale R;Young C.[J].Green Chemistry,2010:1514.
[9]	Darensbourg D J;Holtcamp M W .[J].Coordination Chemistry Reviews,1996,153:155.
[10]	高志文,肖林飞,陈静,夏春谷.二氧化碳与环氧化合物合成环状碳酸酯的研究进展[J].催化学报,2008(09):831-838.
[11]	Church TL;Getzler YDYL;Byrne CM;Coates GW .Carbonylation of heterocycles by homogeneous catalysts[J].Chemical communications,2007(7):657-674.
[12]	Khumtaveeporn K;Alper H .[J].Accounts of Chemical Research,1995,28:414.
[13]	B?ttcher T;Sieber S A .[J].Med Chem Commun,2012,3:408.
[14]	Wang Y;Tennyson R L;Romo D .[J].Heterocycles,2004,64:605.
[15]	Pommier A;Pons J M.[J].Synthesis,1993:441.
[16]	Wu J;Yu T L;Chen C T;Lin C C .[J].Coordination Chemistry Reviews,2006,250:602.
[17]	刘建华,陈静.杂环化合物的羰基化反应[J].化学进展,2004(06):989-999.
[18]	Drent E;Kragtwijk E .[P].EP 577206,1994.
[19]	Lee J T;Thomas P J;Alper H .[J].Journal of Organic Chemistry,2001,66:5424.
[20]	Molnar F;Luinstra G A;Allmendinger M;Reiger B .[J].Chemistry-A European Journal,2003,9:1273.
[21]	Allmendinger M;Eberhardt R;Luinstra G A;Molnar F Rieger B .[J].Zeitschrift Fur Anorganische Und Allgemeine Chemie,2003,629:1347.
[22]	Getzler Y D Y L;Mahadevan V;Lobkovsky E B;Coates G W .[J].Journal of the American Chemical Society,2002,124:1174.
[23]	Mahadevan V;Getzler Y D Y L;Coates G W .[J].Angewandte Chemie International Edition,2002,41:2781.
[24]	Schmidt J A R;Mahadevan V;Getzler Y D Y L;Coates G W .[J].Organic Letters,2004,6:373.
[25]	Getzler Y D Y L;Mahadevan V;Lobkovsky E B;Coates G W .[J].Pure and Applied Chemistry,2004,76:557.
[26]	Schmidt, JAR;Lobkovsky, EB;Coates, GW .Chromium(III) octaethylporphyrinato tetracarbonylcobaltate: A highly active, selective, and versatile catalyst for epoxide carbonylation[J].Journal of the American Chemical Society,2005(32):11426-11435.
[27]	Kramer JW;Lobkovsky EB;Coates GW .Practical beta-lactone synthesis: Epoxide carbonylation at 1 atm[J].Organic letters,2006(17):3709-3712.
[28]	Ganji, P.;Doyle, D.J.;Ibrahim, H. .In situ generation of the coates catalyst: A practical and versatile catalytic system for the carbonylation of meso-epoxides[J].Organic letters,2011(12):3142-3145.
[29]	Chen, Q.;Mulzer, M.;Shi, P.;Beuning, P.J.;Coates, G.W.;O'Doherty, G.A. .De novo asymmetric synthesis of fridamycin e[J].Organic letters,2011(24):6592-6595.
[30]	Stirling A;Iannuzzi M;Parrinello M;Molnar F;Bernhart V;Luinstra GA .beta-Lactone synthesis from epoxide and CO: Reaction mechanism revisited[J].Organometallics,2005(10):2533-2537.
[31]	Church TL;Getzler YDYL;Coates GW .The mechanism of epoxide carbonylation by [Lewis acid](+)[Co(CO)(4)](-) catalysts - art. no. JA061503T[J].Journal of the American Chemical Society,2006(31):10125-10133.
[32]	Kramer J W;Joh D Y;Coates G W .[J].Organic Letters,2007,9:5581.
[33]	Getzler Y D Y L;Kundnani V;Lobkovsky E B;Coates G W .[J].Journal of the American Chemical Society,2004,126:6842.
[34]	Rowely J M;Lobkovsky E B;Coates G W .[J].Journal of the American Chemical Society,2007,129:4948.
[35]	Furukawa J;Iseda H;Saegusa T;Fujii H .[J].Die Makromolekulare Chemie,1965,89:263.
[36]	Takeuchi D.;Sakaguchi Y.;Osakada K. .Alternating copolymerization of propylene oxide with carbon monoxide catalyzed by Co complex and Co/Ru complexes[J].Journal of Polymer Science, Part A. Polymer Chemistry,2002(24):4530-4537.
[37]	Lee J T;Alper H .[J].Macromolecules,2004,37:2417.
[38]	Allmendinger M;Eberhardt R;Luinstra G A;Rieger B .[J].Journal of the American Chemical Society,2002,124:5646.
[39]	Allmendinger M;Eberhardt R;Luinstra G A;Rieger B .[J].Macromolecular Chemistry and Physics,2003,204:564.
[40]	Nakano K;Fumitaka K;Nozaki K .Synthesis of a polyester macromonomer via the cobalt-catalyzed alternating copolymerization of propylene oxide and carbon monoxide[J].Journal of Polymer Science, Part A. Polymer Chemistry,2004(18):4666-4670.
[41]	Liu G;Jia L .[J].Journal of the American Chemical Society,2004,126:14716.
[42]	Allmendinger M.;Zintl M.;Eberhardt R.;Luinstra GA.;Molnar F.;Rieger B. .Online ATR-IR investigations and mechanistic understanding of the carbonylation of epoxides - the selective synthesis of lactones or polyesters from epoxides and CO[J].Journal of Organometallic Chemistry,2004(5):971-979.
[43]	Allmendinger M;Molnar F;Zintl M;Luinstra G A Preishuber-Pflügl P Rieger B .[J].Chemistry-A European Journal,2005,11:5327.
[44]	Brulé, E.;Guo, J.;Coates, G.W.;Thomas, C.M. .Metal-catalyzed synthesis of alternating copolymers[J].Macromolecular rapid communications: Publishing the newsletters of the European Polymer Federation,2011(2):169-185.
[45]	Reichardt R;Rieger B .[J].Advances in Polymer Science,2012,245:49.
[46]	Dunn, E.W.;Coates, G.W. .Carbonylative polymerization of propylene oxide: A multicatalytic approach to the synthesis of poly(3-Hydroxybutyrate)[J].Journal of the American Chemical Society,2010(33):11412-11413.
[47]	Roos L;Goetz R W;Orchin M .[J].Journal of Organic Chemistry,1965,30:3023.
[48]	Rosenthal A;Kan G .[J].Tetrahedron Letters,1967,8:477.
[49]	Powell J B;Mullin S B;Weider P R;Eubanks D C Arhan-cet J P .[P].US 5770776,1998.
[50]	Lee B N;Yang D J;Byun Y H .[P].US 6348611,2002.
[51]	Hamada K;Baba K;Hagihara N .[J].Memoirs Inst Sci Ind Res Osaka Univ,1957,14:207.
[52]	Lenel P O.[J].Proc Chem Soc,1958:50.
[53]	Yokokawa C;Watanabe Y;Takegami Y .[J].Bulletin of the Chemical Society of Japan,1964,37:677.
[54]	Weber R;Englert U;Ganter B;Keim W,M?thrath M.[J].Chemical Communications,2000:1419.
[55]	Nakano K;Katayama M;Ishihara S;Hiyama T;Nozaki K .An alternative route to protected aldols: Cobalt-catalyzed hydroformylation of epoxides and in situ protection of beta-hydroxyaldehydes by HC(OMe)(3)[J].Synlett,2004(8):1367-1370.
[56]	Seki Y;Murai S;Yamamoto I;Sonoda N .[J].Angewandte Chemie International Edition,1977,16:789.
[57]	Tsuji Y;Kobayashi M;Okuda F;Watanabe Y.[J].Journal of the Chemical Society,Chemical Communications,1989:1253.
[58]	Watanabe Y;Nishiyama K;Zhang K;Okuda F Kondo T Tsuji Y .[J].Bulletin of the Chemical Society of Japan,1994,67:879.
[59]	Goodman S N;Jacobsen E N .[J].Angewandte Chemie International Edition,2002,41:4703.
[60]	Eisenmann J;Yamartino R;Howard J .[J].Journal of Organic Chemistry,1961,26:2102.
[61]	McClure J D;Fisher R F .[P].US 3260738,1966.
[62]	Kawabata Y;Tanaka M;Hayashi T;Ogata I .[J].Nippon Kagaku Kaishi,1979,5:635.
[63]	Lee B N;Chen B S .[P].US 6348632,2002.
[64]	Hinterding K;Jacobsen E N .[J].Journal of Organic Chemistry,1999,64:2164.
[65]	Balázs A;Benedek C;Szalontai G;Tor?s S .[J].Steroids,2004,69:271.
[66]	Kim H S;Bae J Y;Lee J S;Jeong II C Choi D K Kang S O Cheong M .[J].Applied Catalysis A:General,2006,301:75.
[67]	Liu J H;Chen J;Xia Ch G .[J].Journal of Molecular Catalysis A:Chemical,2006,250:232.
[68]	Liu J H;Wu H;Xu L W;Chen J Xia Ch G .[J].Journal of Molecular Catalysis A:Chemical,2007,269:97.
[69]	Denmark S E;Ahmad M .[J].Journal of Organic Chemistry,2007,72:9630.
[70]	Deng FG;Hu B;Sun W;Chen J;Xia CG .Novel pyridinium based cobalt carbonyl ionic liquids: synthesis, full characterization, crystal structure and application in catalysis[J].Dalton transactions: An international journal of inorganic chemistry,2007(38):4262-4267.
[71]	Lü Z G;Wang H S;Li J A;Guo Z M .[J].Research on Chemical Intermediates,2010,36:1027.
[72]	Hamasaki A;Muto A;Haraguchi S;Liu X Sakakibara T Yokoyama T Tokunaga M .[J].Tetrahedron Letters,2011,52:6869.

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环氧化合物羰基化反应研究新进展

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