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钯和铜催化的脂肪醇和芳基卤代烃偶联反应
金小平1*, 张莉3, 高浩其2, 房江华2, 李瑞丰3, 方烨汶2,4*
化学进展 ›› 2013, Vol. 25 ›› Issue (11) :1898-1905
钯和铜催化的脂肪醇和芳基卤代烃偶联反应
金小平1*, 张莉3, 高浩其2, 房江华2, 李瑞丰3, 方烨汶2,4*
化学进展 ›› 2013, Vol. 25 ›› Issue (11) :1898-1905
钯和铜催化的脂肪醇和芳基卤代烃偶联反应
Palladium- and Copper-Catalyzed Cross Coupling Reaction of Aliphatic Alcohols and Aryl Halides
烷基芳基醚广泛存在于天然产物和药物分子中。钯和铜催化构筑C—O键的方法已成为合成烷基芳基醚的有效策略。本文总结了钯和铜催化的脂肪醇芳基化反应的最新研究进展。 以Buchwald小组发展的基于联苯骨架的二叔丁基取代单膦配体, Hartwig小组发展的基于五苯基取代的二茂铁骨架的二叔丁基取代单膦配体或 Beller小组发展的基于二吡唑骨架的二金刚烷基取代的单膦配体,可高效实现钯催化的各类脂肪醇和芳基卤代烃的C—O偶联。 在铜催化反应条件下,1,10-菲罗啉及其衍生物和β-二羰基化合物是反应活性最高的两类配体。 总的来说,和铜催化条件相比,钯催化的C—O偶联反应具有反应条件温和,官能团兼容性好,底物普适性广等优点。 此外,对两类催化体系在配体选用、反应活性、β-H消除反应和反应机理等方面的差异进行了探讨。 设计与合成新型配体被认为是C—O偶联反应取得进一步发展的关键。
Alkyl aryl ethers are present in many naturally occurring and medicinally relevant compounds. Palladium- and copper-catalyzed C—O bond formation reactions have become effective strategies for their preparation. Recent developments in palladium- and copper-catalyzed arylations of aliphatic alcohols are summarized in this review. Palladium-catalyzed C—O cross coupling of various aliphatic alcohols with aryl halides could be efficiently realized in the presence of di-tert-buthyl biarylphosphine ligand, di-tert-buthylphosphino pentaphenylferrocene ligand, or di-adamantyl-substituted Bippyphos ligand developed by Buchwald, Hartwig, and Beller groups respectively. With the copper catalyst, 1, 10-phenanthroline and its derivatives, β-dicarbonyl compounds were served as the most efficient ligands. Generally, palladium-catalyzed C—O cross-coupling reactions display mild reaction conditions, good functional-group compatability, and broad substrate scope compared to the copper catalyst system. Moreover, the difference of the two catalytic systems including the choice of ligand, reactivity, β-H elimination and mechanism is discussed. The design and synthesis of new ligands are the key point for the further development of the C—O cross coupling.
Contents
1 Introduction
2 Pd-catalzyed arylation of alphatic alcohols
3 Cu-catalyzed arylation of alphatic alcohols
3.1 Cu-catalyzed C—O cross coupling reaction without ligand
3.2 Cu-catalyzed C—O cross coupling reaction in the presence of ligand
4 Comparative studies of two catalysts
4.1 Choice of ligands
4.2 Catalytic activity
4.3 β-H elimination reaction
4.4 Reaction mechanism
5 Conclusion and outlook
烷基芳基醚
alkyl aryl ethers
[1] Diederich F, Meijere A. Metal-Catalyzed Cross-Coupling Reactions. Weinheim: Wiley-VCH, 2004
[2] Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev., 2002, 102 (5): 1359—1470
[3] Miyaura N. Topics in Current Chemistry. Vol. 219. New York: Springer-Verlag, 2002
[4] Frlan R, Kikelj D. Synthesis, 2006, (14): 2271—2285
[5] 于海珠 (Yu H Z), 傅尧 (Fu Y), 白小宇 (Bai X Y), 郭庆祥 (Guo Q X). 化学进展 (Progress in Chemsitry), 2010, 22 (4): 557—572
[6] Sawyer J S. Tetrahedron, 2000, 56 (29): 5045—5065
[7] Enthaler S, Company A. Chem. Soc. Rev., 2011, 40 (10): 4912—4924
[8] Palucki M, Wolfe J P, Buchwald S L. J. Am. Chem. Soc., 1996, 118 (42): 10333—10334
[9] Mann G, Hartwig J F. J. Am. Chem. Soc., 1996, 118 (51): 13109—13110
[10] Mann G, Incarvito C, Rheingold A L, Hartwig J F. J. Am. Chem. Soc., 1999, 121 (13): 3224—3225
[11] Shelby Q, Kataoka N, Mann G, Hartwig J F. J. Am. Chem. Soc., 2000, 122 (43): 10718—10719
[12] Kataoka N, Shelby Q, Stambuli J P, Hartwig J F. J. Org. Chem., 2002, 67 (16): 5553—5566
[13] Torraca K E, Kuwabe S I, Buchwald S L. J. Am. Chem. Soc., 2000, 122 (51): 12907—12908
[14] Kuwabe S I, Torraca K E, Buchwald S L. J. Am. Chem. Soc., 2001, 123 (49): 12202—12206
[15] Vorogushin A V, Huang X, Buchwald S L. J. Am. Chem. Soc., 2005, 127 (22): 8146—8149
[16] Singer R A, Doré M, Sieser J E, Berliner M A. Tetrahedron Lett., 2006, 47 (22): 3727—3731
[17] Withbroe G J, Singer R A, Sieser J E. Org. Process. Res. Dev., 2008, 12 (3): 480—489
[18] Gowrisankar S, Sergeev A G, Anbarasan P, Spannenberg A, Neumann H, Beller M. J. Am. Chem. Soc., 2010, 132 (33): 11592—11598
[19] Gowrisankar S, Neumann H, Beller M. ChemCatChem, 2011, 3 (9): 1439—1441
[20] Gowrisankar S, Neumann H, Beller M. Chem. Eur. J., 2012, 18 (9): 2498—2502
[21] Wu X, Fors B P, Buchwald S L. Angew. Chem. Int. Ed., 2011, 50 (42): 9943—9947
[22] Hoshiya N, Buchwald S L. Adv. Synth. Catal., 2012, 354 (10): 2031—2037
[23] Zhu R, Buchwald S L. Angew. Chem. Int. Ed., 2012, 51 (8): 1926—1929
[24] Dash P, Janni M, Peruncheralathan S. Eur. J. Org. Chem., 2012, (26): 4914—4917
[25] Maligres P E, Li J, Krska S W, Schreier J D, Raheem I T. Angew. Chem. Int. Ed., 2012, 51 (36): 9071—9074
[26] Watanabe M, Nishivama M, Koie Y. Tetrahedron Lett., 1999, 40 (50): 8837—8840
[27] Ylijoki K E O, Kündig E P. Chem. Commun., 2011, 47 (38): 10608—10610
[28] Jing X B, Yan C G, Sun J, Wang L, An L. Chin. Chem. Lett., 2004, 15 (12): 1392—1394
[29] Neogi A, Majhi T P, Achari B, Chattopadhyay P. Eur. J. Org. Chem., 2008, (2): 330—336
[30] Bhattacharya D, Behera A, Hota S K, Chattopadhyay P. Synthesis, 2011, (4): 585—592
[31] Khoumeri O, Crozet M D, Terme T, Vanelle P. Tetrahedron Lett., 2009, 50 (46): 6372—6376
[32] Meng T, Zhang W X, Zhang H J, Liang Y, Xi Z. Synthesis, 2012, 44 (17): 2754—2762
[33] Ullmann F. Chem. Ber., 1904, 37: 853—854
[34] Lindley J. Tetrahedron, 1984, 40 (9): 1433—1456
[35] Chan D M T, Monaco K L, Wang R P, Winters M P. Tetrahedron Lett., 1998, 39 (19): 2933—2936
[36] Lam P Y S, Clark C G, Saubern S, Adams J, Winters M P, Chan D M T, Combs A. Tetrahedron Lett., 1998, 39 (19): 2941—2944
[37] Rao K S, Wu T S. Tetrahedron, 2012, 68 (38): 7735—7754
[38] Quach T D, Batey R A. Org. Lett., 2003, 5 (8): 1381—1384
[39] Lam P Y S, Vincent G, Bonne D, Clark C G. Tetrahedron Lett., 2003, 44 (26): 4927—4931
[40] Mondal M, Sarmah G, Gogoi K, Bora U. Tetrahedron Lett., 2012, 53 (46): 6219—6222
[41] Sicé J. J. Am. Chem. Soc., 1953, 75 (15): 3697—3700
[42] Keegstra M A, Peters T H A, Brandsma L. Tetrahedron, 1992, 48 (17): 3633—3652
[43] Basu B, Das S, Mandal B. Indian J. Chem. Sect B, 2008, 47B (11): 1701—1706
[44] Aalten H L, van Koten G, Grove D M, Kuilman T, Piekstra O G, Hulshof L A, Sheldon R A. Tetrahedron, 1989, 45 (17): 5565—5578
[45] Amberg W, Bennani Y L, Chadha R K, Crispino G A, Davis W D, Hartung J, Jeong K S, Ogino Y, Shibata T, Sharpless K B. J. Org. Chem., 1993, 58 (4): 844—849
[46] Huang J K, Chen Y, Chan J, Ronk M L, Larsen R D, Faul M M. Synlett, 2011, (10): 1419—1422
[47] Zhu J Y, Price B A, Zhao S X, Skonezny P M. Tetrahedron Lett., 2000, 41 (21): 4011—4014
[48] Bovicelli P, Antonioletti R, Onori A, Delogu G, Fabbri D, Dettori M A. Tetrahedron, 2006, 62 (4): 635—639
[49] Maiti D. Chem. Commun., 2011, 47 (29): 8340—8342
[50] Ley S V, Thomas A W. Angew. Chem. Int. Ed., 2003, 42 (44): 5400—5449
[51] Beletskaya I P, Cheprakov A V. Coord. Chem. Rev., 2004, 248 (21/24): 2337—2364
[52] Sadig J E R, Willis M C. Synthesis, 2011, (1): 1—22
[53] Dehli J R, Legros J, Bolm C. Chem. Commun., 2005, (8): 973—986
[54] Fang Y W, Li C Z. Chem. Commun., 2005, (28): 3574—3576
[55] Fang Y W, Li C Z. J. Org. Chem., 2006, 71 (17): 6427—6431
[56] Fagan P J, Hauptman E, Shapiro R, Casalnuovo A. J. Am. Chem. Soc., 2000, 122 (21): 5043—5051
[57] Wolter M, Nordmann G, Job G E, Buchwald S L. Org. Lett., 2002, 4 (6): 973—976
[58] Job G E, Buchwald S L. Org. Lett., 2002, 4 (21): 3703—3706
[59] Bao W L, Liu Y Y, Lv X, Qian W X. Org. Lett., 2008, 10 (17): 3899—3902
[60] Liu Y Y, Bao W L. Org. Biomol. Chem., 2010, (12): 2700—2703
[61] Hosseinzadeh R, Tajbakhsh M, Mohadjerani M, Alikarami M. Synlett, 2005, (7): 1101—1104
[62] Dibakar M, Prakash A, Selvakumar K, Ruckmani K, Sivakumar M. Tetrahedron Lett., 2011, 52 (41): 5338—5341
[63] Fang Y W, Li C Z. J. Am. Chem. Soc., 2007, 129 (26): 8092—8093
[64] Altman R A, Shafir A, Chio A, Lichtor P A, Buchwald S L. J. Org. Chem., 2007, 73 (1): 284—286
[65] Nordmann G, Buchwald S L. J. Am. Chem. Soc., 2003, 125 (17): 4978—4979
[66] Polaske N W, Szalai M L, Shanahan C S, McGrath D V. Org. Lett., 2010, 12 (21): 4944—4947
[67] Shafir A, Lichtor P A, Buchwald S L. J. Am. Chem. Soc., 2007, 129 (12): 3490—3491
[68] Jones G O, Liu P, Houk K N, Buchwald S L. J. Am. Chem. Soc., 2010, 132 (17): 6205—6213
[69] Yu H Z, Jiang Y Y, Fu Y, Liu L. J. Am. Chem. Soc., 2010, 132 (51): 18078—18091
[70] Zhang H, Ma D W, Cao W G. Synlett, 2007, (2): 243—246
[71] Niu J J, Zhou H, Li Z G, Xu J W, Hu S J. J. Org. Chem., 2008, 73 (19): 7814—7817
[72] Niu J J, Guo P, Kang J T, Li Z G, Xu J W, Hu S J. J. Org. Chem., 2009, 74 (14): 5075—5078
[73] Vuluga D, Legros J, Crousse B, Bonnet-Delpon D. Eur. J. Org. Chem., 2009, (21): 3513—3518
[74] Maligres P E, Krska S W, Dormer P G. J. Org. Chem., 2012, 77 (17): 7646—7651
[75] Widenhoefer R A, Zhong H A, Buchwald S L. J. Am. Chem. Soc., 1997, 119 (29): 6787—6795
[76] Widenhoefer R A, Buchwald S L. J. Am. Chem. Soc., 1998, 120 (26): 6504—6511
[77] Aranyos A, Old D W, Kiyomori A, Wolfe J P, Sadighi J P, Buchwald S L. J. Am. Chem. Soc., 1999, 121 (18): 4369—4378
[78] Giri R, Hartwig J F. J. Am. Chem. Soc., 2010, 132 (45): 15860—15863
[79] Beletskaya I P, Cheprakov A V. Organometallics, 2012, 31 (22): 7753—7808
[80] Monnier F, Taillefer M. Angew. Chem. Int. Ed., 2009, 48 (38): 6954—6971
[81] Chen C Y, Weisel M. Synlett, 2013, 24 (2): 189—192
[82] Manbeck G F, Lipman A J, Stockland R A Jr, Freidl A L, Hasler A F, Stone J J, Guzei I A. J. Org. Chem., 2005, 70 (1): 244—250
[83] Mehmood A, Denine W G, Leadbeater N E. Top. Catal., 2010, 53 (15/18): 1073—1080
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