OALib Journal期刊
非官能化芳烃与烯烃的直接氧化偶联反应
, PP. 523-544
Keywords: Fujiwara-Moritani反应 ,直接氧化偶联 ,氧化Heck反应 ,烯烃化 ,芳基化 ,C-H官能化
Abstract:
芳基烯烃是一类具有重要应用价值的化合物,其合成方法已被广泛研究。目前,过渡金属催化非官能化芳烃与烯烃的直接氧化偶联反应是构造芳基烯烃最高效、最简捷的方法,同Heck偶联反应相比,其底物无需预先官能化,这不仅大大缩短了反应步骤,并且能从源头上杜绝废盐的产生,特别是当以氧气或空气作氧化剂时,副产物仅为水,不会对环境造成任何危害。该方法同传统制备芳基烯烃的诸多方法相比具有原子利用率高、原子经济性好和环境友好等绿色化学的典型特性。本文根据催化剂的种类、底物类型及导向基类型对近年来过渡金属催化非官能化芳烃与烯烃的直接偶联反应进行了分类详述,并对若干重要体系的反应机理进行了详细讨论。
References
[1] Tan K, Rozas E G, Bon R S, Guo Z, Delon C, Wetzel S, Arndt S, Alexandrov K, Waldmann H, Goody R S, Wu Y, Blankenfeldt W. J. Med. Chem., 2009, 52: 8025-8037 [2] Singh J, Zeller W, Zhou N, Hategan G, Mishra R K, Polozov A, Yu P, Onua E, Zhang J, Ramirez J L, Sigthorsson G, Thorsteinnsdottir M, Kiselyov A S, Zembower D E, Andresson T, Gurney M E. J. Med. Chem., 2010, 53: 18-36 [3] Lee L, Robb L M, Lee M, Davis R, Mackay H, Chavda S, Babu B, Brien E L, Risinger A L, Mooberry S L, Lee M. J. Med. Chem., 2010, 53: 325-334 [4] Shen C, Ni C, Shen Y, Huang Y, Kuo C, Wu T, Chen C. J. Nat. Prod., 2009, 72: 168-171 [5] Kingston D. J. Nat. Prod., 2009, 72: 507-515 [6] Kwak G, Kim S, Fujiki M, Masuda T, Kawakami Y, Aoki T. Chem. Mater., 2004, 16: 1864-1868 [7] Takahashi M, Nishide H, Tsuchida E, Lahti P M. Chem. Mater., 1997, 9: 11-13 [8] Beletskaya I P, Cheprakov A V. Chem. Rev., 2000, 100: 3009-3066 [9] Dounay A B, Overman L E., Chem. Rev., 2003, 103: 2945-2963 [10] Moritani I, Fujiwara Y. Tetrahedron Lett., 1967, 8: 1119-1122 [11] Fujiwara Y, Moritani I, Matsuda M. Tetrahedron, 1968, 24: 4819-4824 [12] Danno S, Moritani I, Fujiwara Y. Tetrahedron, 1969, 25: 4809-4813 [13] Fujiwara Y, Moritani I, Asano R, Tanaka H, Teranishi S. Tetrahedron, 1969, 25: 4815-4818 [14] Moritani I, Fujiwara Y. Synthesis, 1973: 524-533 [15] Yokota T, Tani M, Sakaguchi S, Ishii Y. J. Am. Chem. Soc., 2003, 125: 1476-1477 [16] Zhang Y, Shi B, Yu J. J. Am. Chem. Soc., 2009, 131: 5072-5073 [17] Zhang X, Fan S, He C, Wan X, Min Q, Yang J, Jiang Z. J. Am. Chem. Soc., 2010, 132: 4506-4507 [18] Mikami K, Hatano M, Terada M. Chem. Lett., 1999, 30: 55-56 [19] Thiery E, Harakat D, Bras J L, Muzart J. Organometallics, 2008, 27: 3996-4004 [20] Aouf C, Thiery E, Bras J L, Muzart J. Org. Lett., 2009, 11: 4096-4099 [21] Zhao J, Huang L, Cheng K, Zhang Y. Tetrahedron Lett., 2009, 50: 2758-2761 [22] Jiang H, Feng Z, Wang A, Liu X, Chen Z. Eur. J. Org. Chem., 2010, 1227-1230 [23] Miura M, Tsuda T, Satoh T, Pivsa-Art S, Nomura M. J. Org. Chem., 1998, 63: 5211-5215 [24] Boele M, Strijidonck G, Vries A, Kamer P, Vries J, Leeuwen P. J. Am. Chem. Soc., 2002, 124: 1586-1587 [25] Lee G T, Jiang X, Prasad K, Repi O, Blacklock T J. Adv. Synth. Catal., 2005, 347: 1921-1924 [26] Amatore C, Cammoun C, Jutand A. Adv. Synth. Catal., 2007, 349: 292-296 [27] Houlden C E, Bailey C D, Ford J G, Gagné M R, Lloyd-Jones G C, Booker-Milburn K I. J. Am. Chem. Soc., 2008, 130: 10066-10067 [28] Miura M, Tsuda T, Satoh T, Nomura M. Chem. Lett., 1997, 26: 1103-1104 [29] Wu J, Cui X, Chen L, Jiang G, Wu Y. J. Am. Chem. Soc., 2009, 131: 13888-13889 [30] Engle K M, Wang D, Yu J. Angew. Chem. Int. Ed., 2010, 49: 6169-6173 [31] Lu Y, Wang D, Engle K M, Yu J. J. Am. Chem. Soc., 2010, 132: 5916-5921 [32] Sasuki K, Sakakura T, Tokunaga, Wada K, Tanaka M. Chem. Lett., 1988, 17: 685-688 [33] Matsumoto T, Yoshida H. Chem. Lett., 2000, 29: 1064-1065 [34] Umeda N, Hirano K, Satoh T, Miura M. J. Org. Chem., 2009, 74: 7094-7099 [35] Chen J, Song G, Pan C, Li X. Org. Lett., 2010, 12: 5426-5429 [36] Wang F, Song G, Li X. Org. Lett., 2010, 12: 5430-5433 [37] Tsai A S, Brasse M, Bergman R G, Ellman J A. Org. Lett., 2011, 13: 540-542 [38] Rakshit S, Grohmann C, Besset T, Glorius F. J. Am. Chem. Soc., 2011, 133: 2350-2353 [39] Ueura K, Satoh T, Miura M. Org. Lett., 2007, 9: 1407-1409 [40] Mochida S, Hirano K, Satoh T, Miura M. Org. Lett., 2010, 12: 5776-5779 [41] Patureau F W, Glorius F. J. Am. Chem. Soc., 2010, 132: 9982-9983 [42] Park S H, Kim J Y, Chang S. Org. Lett., 2011, 13: 2372-2375 [43] Kakiuchi F, Sato T, Yamauchi M, Chatani N, Murai S. Chem. Lett., 1999, 28: 19-20 [44] Kwon K, Lee D W, Yi C S. Organometallics, 2010, 29: 5748-5750 [45] Asano R, Moritani I, Fujiwara Y, Teranishi S. Bull. Chem. Soc. Jpn., 1973, 46: 663-664 [46] Bras J L, Muzart J. Chem. Rev., 2011, 111: 1170-1214 [47] Tsuji J, Nagashima H. Tetrahedron, 1984, 40: 2699-2702 [48] Jia C, Lu W, Kitamura T, Fujiwara Y. Org. Lett., 1999, 1: 2097-2100 [49] Dams M, Vos D, Celen S, Jacobs P. Angew. Chem. Int. Ed., 2003, 42: 3512-3515 [50] Li P, Gu J, Ying Y, He Y, Zhang H, Zhao G, Zhu S. Tetrahedron, 2010, 66: 8387-8391 [51] Miyasaka M, Hirani K, Satoh T, Miura M. J. Org. Chem., 2010, 75: 5421-5424 [52] Grimster N P, Gauntlett C, Godfrey C, Gaunt M J. Angew. Chem. Int. Ed., 2005, 44: 3125-3129 [53] Djakovitch L, Rouge P. J. Mol. Catal. A: Chem., 2007, 273: 230-239 [54] Xu Y, Wang W, Wen Z, Hartley J, Loh T. Tetrahedron Lett., 2010, 51: 3504-3507 [55] Yang Y, Chen L, Zhang Z, Zhang Y. Org. Lett., 2011, 13: 1342-1345 [56] Zhu C, Falck J R. Org. Lett., 2011, 13: 1214-1217 [57] Cai G, Fu Y, Li Y, Wan X, Shi Z. J. Am. Chem. Soc., 2007, 129: 7666-7673 [58] Li J, Mei T, Yu J. Angew. Chem. Int. Ed., 2008, 47: 6452-6455 [59] García A, Urones B, Arrayás R G, Carretero J C. Chem. Eur. J., 2010, 16: 9676-9685 [60] Horino H, Inoue N. J. Org. Chem., 1981, 46: 4416-4421 [61] Wang J, Yang C, Liu L, Guo Q. Tetrahedron Lett., 2007, 48: 5449-5453 [62] Nishikata T, Lipshutz B H. Org. Lett., 2010, 12: 1972-1975 [63] B？ckvall J, Gogoll A. J. Chem. Soc. Chem. Commun., 1987, 1236-1238 [64] Aoki S, Oyamada J, Kitamura T. Bull. Chem. Soc. Jpn., 2005, 78: 468-472 [65] Cho S H, Hwang S J, Chang S. J. Am. Chem. Soc., 2008, 130: 9254-9256 [66] Shi B, Zhang Y, Lam J K, Wang D, Yu J. J. Am. Chem. Soc., 2010, 132: 460-461 [67] Baran P S, Corey E J. J. Am. Chem. Soc., 2002, 124: 7904-7905 [68] Zhang H, Ferreira E M, Stoltz B M. Angew. Chem. Int. Ed., 2004, 43: 6144-6148 [69] Schiffner JA, W？ste T H, Oestreich M. Eur. J. Org. Chem., 2010, 174-182 [70] Ferreira E M, Stoltz M B. J. Am. Chem. Soc., 2003, 125: 9578-9579 [71] Ueda S, Okada T, Nagasawa H. Chem. Commun., 2010, 2462-2464 [72] Matsumoto T, Yoshida H. Inorg. Chem. Commun., 2001, 4: 365-367 [73] Matsumoto T, Periana R A, Taube D J, Yoshida H. J. Catal., 2002, 206: 272-280 [74] Diamond S E, Szalkiewicz A, Mares F. J. Am. Chem. Soc., 1979, 101: 490-491 [75] Wang F, Song G, Du Z, Li X. J. Am. Chem. Soc., 2011, 76: 2926-2932 [76] Kahiuchi F, Yamauchi M, Chatani N, Murai S. Chem. Lett., 1996, 25: 111-112 [77] Weissman H, Song X, Milstein D. J. Am. Chem. Soc., 2001, 123: 337-338 [78] Guan Z, Yan Z, Ren Z, Liu X, Liang Y. Chem. Commun., 2010, 2823-2825 [79] Bernini R, Fabrizi G, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed., 2009, 48: 8078-8081 [80] Wu C, Tang Z, Fan W, Zhu W, Wang C, Somoza E, Owino N, Li R, Ma P C, Wang Y. J. Med. Chem., 2010, 53: 139-146 [81] Xue H, Lu X, Zheng P, Liu L, Han C, Hu J, Liu Z, Ma T, Li Y, Wang L, Chen Z, Liu G. J. Med. Chem., 2010, 53: 1397-1401 [82] Kesting J R, Tolderlund I, Pedersen A F, Witt M, Jaroszewski J W, Staerk D. J. Nat. Prod., 2009, 72: 312-315 [83] Pettit G R, Thornhill A, Melody N, Knight J C. J. Nat. Prod., 2009, 72: 380-388 [84] Fujiwara Y, Moritani I, Matsuda M, Teranishi S., Tetrahedron Lett., 1968, 9: 3863-3865 [85] Fujiwara Y, Moritani I, Matsuda M. Tetrahedron Lett., 1968, 9: 633-636 [86] Danno S, Moritani I, Fujiwara Y. Tetrahedron, 1969, 25: 4819-4823 [87] Fujiwara Y, Moritani I, Asano R, Teranishi S. Tetrahedron Lett., 1968, 9: 6015-6017 [88] Fujiwara Y, Moritani I, Danno S, Asano R, Teranishi S. J. Am. Chem. Soc., 1969, 91: 7166-7169 [89] Asano R, Moritani I, Sonoda A, Fujiwara Y, Teranishi S. J. Chem. Soc. (C), 1971, 3691-3692
Full-Text
Contact Us
service@oalib.com
QQ:3279437679
WhatsApp +8615387084133
