环钯化合物合成及其在催化中的应用
|
摘要
环钯化合物由于丰富的结构、高度的稳定性和卓越的催化性能,已成为钯化学研究的热点之一。迄今已开发出了C-H键活化、氧化加成、转金属化、亲核加成和配体交换等多种方法,可制备出从三元环到十一元环的CY型环钯化合物和多种YCY型环钯化合物。环钯化合物目前已应用于偶联、烯烃氢化和不对称催化等反应中。本文简单介绍了环钯化合物的种类,重点介绍了环钯化合物的合成方法和催化应用情况,最后提出了环钯化合物在今后合成研究和催化应用中的发展建议。
Due to their abundant structures,high stability and excellent catalytic properties,palladacycles complexes have become one of the hotspots in the research of palladium chemistry. A number of synthesis methods have been developed,such as C-H bond activation,oxidation addition,metal transfer,nucleophilic addition,and ligand exchange. The CY type palladacycles complexes from ternary ring to eleven-membered ring and YCY type palladacycles complexes have been afforded. Palladacycles complexes have been utilized in olefin hydrogenation,coupling reaction,asymmetric catalysis,and other reactions. In this article,the types of palladacycles complexes were briefly introduced. The synthesis methods and application for catalytic reactions of palladacycles complexes were focused on. The development suggestions of palladacycles complexes for synthesis and catalytic application were proposed.
Due to their abundant structures,high stability and excellent catalytic properties,palladacycles complexes have become one of the hotspots in the research of palladium chemistry. A number of synthesis methods have been developed,such as C-H bond activation,oxidation addition,metal transfer,nucleophilic addition,and ligand exchange. The CY type palladacycles complexes from ternary ring to eleven-membered ring and YCY type palladacycles complexes have been afforded. Palladacycles complexes have been utilized in olefin hydrogenation,coupling reaction,asymmetric catalysis,and other reactions. In this article,the types of palladacycles complexes were briefly introduced. The synthesis methods and application for catalytic reactions of palladacycles complexes were focused on. The development suggestions of palladacycles complexes for synthesis and catalytic application were proposed.
引文
[1]陈新兵,安忠维.应用化工,2000,29(03):3~5+11.
[2]钟艳辉,丁皓,冯建.应用化工,2017,46(06):1051~1054.
[3]王文涛,刘小民,张生军等.应用化工,2010,39(01):116~121.
[4] R B Bedford. Chem. Commun.,2003,(15):1787~1796.
[5] I P Beletskaya,A V Cheprakov. J. Organomet. Chem.,2004,689(24):4055~4082.
[6] J Dupont,C S Consorti,J Spencer. Chem. Rev.,2005,105(6):2527~2571.
[7] A C Cope,E C Friedrich. J. Am. Chem. Soc.,1968,90(4):909~911.
[8] J Dupont,M Pfeffer,J Spencer. Eur. J. Inorg. Chem.,2001,(8):1917~1927.
[9] D Sole,L Vallverdu,X Solans et al. J. Am. Chem. Soc.,2003,125(6):1587~1594.
[10] D Zim,S L Buchwald. Org. Lett.,2003,5(14):2413~2415.
[11] D Morales-Morales, R Redon, C Yung et al. Chem.Commun.,2000,(17):1619~1634.
[12] S G Koller, R Martín-Romo, J S Melero et al.Organometallics,2014,33(24):7329~7332.
[13] M Oliva-Madrid, J García-López, I Saura-Llamas et al.Organometallics,2014,33(22):6420~6430.
[14] G Ebeling, M R Meneghetti, F Rominger et al.Organometallics,2002,21(15):3221~3227.
[15] S Molitor,C Schwarz,V H Gessner. Organometallics,2016,35(2):159~167.
[16] C S Consorti,G Ebeling,F Rodembusch et al. Inorg. Chem.,2004,43(2):530~536.
[17]张圆圆,夏玲浩,曹源等.合成化学,2014,22(03):341~345.
[18] E A B Kantchev,G Peh,C Zhang. Org. Lett.,2008,10(8):3949~3952.
[19] E A B Kantchev,J Y Ying. Organometallics,2009,28(1):289~299.
[20] Y Kong,L Wen,H Song et al. Organometallics,2011,30(1):153~159.
[21]李敬亚,吴养洁,韩自省等.高等学校化学学报,2008,(8):1555~1559.
[22] M Li,H Song,B Wang. Organometallics,2015,34(10):1969~1977.
[23]夏玲浩,张圆圆,曹源等.合成化学,2014,22(4):496~498.
[24]郭孟萍,周丽,何仁.应用化学,2006,(05):480~483.
[25]赵雪梅,赵海沨,牛俊龙等.化学通报,2008,71(4):281~285.
[26] L Dang,H Song,B Wang. Organometallics,2014,33(23):6812~6818.
[27] S Sara,A M Jose,P Eduardo. Organometallics,2013,32(4):1112~1120.
[28]杨亮茹,张金莉,宋毛平等.化学学报,2003,(07):959~962.
[29]索全伶,张丹昭,柯春龙等.高等学校化学学报,2016,37(3):552~558.
[30]王炯,穆兵,付志华等.催化学报,2014,35(7):1059~1067.
[31]李耀华,陈兵,徐寿颐.应用化工,2001,(6):25~28.
[32]徐启杰,崔元臣,陈慧卿等.应用化工,2008,(9):1010~1014.
[33] M Liu,P Yang,M K Karunananda et al. J. Am. Chem. Soc.,2018,140(17):5805~5813.
[34] M Nowotny, U Hanefeld, H Koningsveld et al. Chem.Commun.,2000,(19):1877~1878.
[35] X Gai,R Grigg,M I Ramzan et al. Chem. Commun.,2000,(20):2053~2054.
[36] I S Viacheslav.有机化学,2018,38(1):75~85.
[37] M L O’Duill,R Matsuura,Y Wang et al. J. Am. Chem.Soc.,2017,139(44):15576~15579.
[38] P K Santra,C R Saha. J. Mol. Catal.,1987,39(3):279~292.
[39] A Bose,C R Saha. J. Mol. Catal.,1989,49(3):271~283.
[40] D Morales-Morales, R Redon, C Yung et al. Chem.Commun.,2000,(17):1619~1670.
[41] D A Lonso,C Nejera,M C Pacheco. Org. Lett.,2000,2(13):1823~1826.
[42] D E Bergbreiter,P L Osburn,A Wilson et al. J. Am. Chem.Soc.,2000,122(38):9058~9064.
[43] A S Gruber,D Zim,G Ebeling et al. Org. Lett.,2000,2(9):1287~1290
[44] D Zim,A S Gruber,G Ebeling et al. Org. Lett.,2000,2(18):2881~2884.
[45] X Gai,R Grigg,M I Ramzan et al. Chem. Commun.,2000,(20):2053~2054.
[46] S Darses,G Michaud,J P Genet. Eur. J. Org. Chem.,1999,(8):1875~1883.
[47] M S Viciu,R A III Kelly,E D Stevens et al. Org. Lett.,2003,5(9):1479~1482.
[48] G D Frey,J Schütz,E Herdtweck et al. Organometallics,2005,24(18):4416~4426.
[49] O Navarro,N Marion,Y Oonishi et al. J. Org. Chem.,2006,71(2):685~692.
[50] L Jin,W Wei,N Sun et al. Org. Chem. Front.,2018,5(16):2484~2491.
[51] J Broggi,H Clavier,S P Nolan. Organometallics,2008,27(21):5525~5531.
[52] B Alexandre,R Maxime,M Alami et al. ACS Catal.,2015,5(2):1386~1396.
[53] N Marion,S P Nolan. Acc. Chem. Res.,2008,41(11):1440~1449.
[54] R Navarro,E P Urriolabeitia,C Cativiela et al. J. Mol. Catal.A,1996,105(3):111~116.
[55] M A Stark,G Jones,C J Richards. Organometallics,2000,19(7):1282~1291.
[2]钟艳辉,丁皓,冯建.应用化工,2017,46(06):1051~1054.
[3]王文涛,刘小民,张生军等.应用化工,2010,39(01):116~121.
[4] R B Bedford. Chem. Commun.,2003,(15):1787~1796.
[5] I P Beletskaya,A V Cheprakov. J. Organomet. Chem.,2004,689(24):4055~4082.
[6] J Dupont,C S Consorti,J Spencer. Chem. Rev.,2005,105(6):2527~2571.
[7] A C Cope,E C Friedrich. J. Am. Chem. Soc.,1968,90(4):909~911.
[8] J Dupont,M Pfeffer,J Spencer. Eur. J. Inorg. Chem.,2001,(8):1917~1927.
[9] D Sole,L Vallverdu,X Solans et al. J. Am. Chem. Soc.,2003,125(6):1587~1594.
[10] D Zim,S L Buchwald. Org. Lett.,2003,5(14):2413~2415.
[11] D Morales-Morales, R Redon, C Yung et al. Chem.Commun.,2000,(17):1619~1634.
[12] S G Koller, R Martín-Romo, J S Melero et al.Organometallics,2014,33(24):7329~7332.
[13] M Oliva-Madrid, J García-López, I Saura-Llamas et al.Organometallics,2014,33(22):6420~6430.
[14] G Ebeling, M R Meneghetti, F Rominger et al.Organometallics,2002,21(15):3221~3227.
[15] S Molitor,C Schwarz,V H Gessner. Organometallics,2016,35(2):159~167.
[16] C S Consorti,G Ebeling,F Rodembusch et al. Inorg. Chem.,2004,43(2):530~536.
[17]张圆圆,夏玲浩,曹源等.合成化学,2014,22(03):341~345.
[18] E A B Kantchev,G Peh,C Zhang. Org. Lett.,2008,10(8):3949~3952.
[19] E A B Kantchev,J Y Ying. Organometallics,2009,28(1):289~299.
[20] Y Kong,L Wen,H Song et al. Organometallics,2011,30(1):153~159.
[21]李敬亚,吴养洁,韩自省等.高等学校化学学报,2008,(8):1555~1559.
[22] M Li,H Song,B Wang. Organometallics,2015,34(10):1969~1977.
[23]夏玲浩,张圆圆,曹源等.合成化学,2014,22(4):496~498.
[24]郭孟萍,周丽,何仁.应用化学,2006,(05):480~483.
[25]赵雪梅,赵海沨,牛俊龙等.化学通报,2008,71(4):281~285.
[26] L Dang,H Song,B Wang. Organometallics,2014,33(23):6812~6818.
[27] S Sara,A M Jose,P Eduardo. Organometallics,2013,32(4):1112~1120.
[28]杨亮茹,张金莉,宋毛平等.化学学报,2003,(07):959~962.
[29]索全伶,张丹昭,柯春龙等.高等学校化学学报,2016,37(3):552~558.
[30]王炯,穆兵,付志华等.催化学报,2014,35(7):1059~1067.
[31]李耀华,陈兵,徐寿颐.应用化工,2001,(6):25~28.
[32]徐启杰,崔元臣,陈慧卿等.应用化工,2008,(9):1010~1014.
[33] M Liu,P Yang,M K Karunananda et al. J. Am. Chem. Soc.,2018,140(17):5805~5813.
[34] M Nowotny, U Hanefeld, H Koningsveld et al. Chem.Commun.,2000,(19):1877~1878.
[35] X Gai,R Grigg,M I Ramzan et al. Chem. Commun.,2000,(20):2053~2054.
[36] I S Viacheslav.有机化学,2018,38(1):75~85.
[37] M L O’Duill,R Matsuura,Y Wang et al. J. Am. Chem.Soc.,2017,139(44):15576~15579.
[38] P K Santra,C R Saha. J. Mol. Catal.,1987,39(3):279~292.
[39] A Bose,C R Saha. J. Mol. Catal.,1989,49(3):271~283.
[40] D Morales-Morales, R Redon, C Yung et al. Chem.Commun.,2000,(17):1619~1670.
[41] D A Lonso,C Nejera,M C Pacheco. Org. Lett.,2000,2(13):1823~1826.
[42] D E Bergbreiter,P L Osburn,A Wilson et al. J. Am. Chem.Soc.,2000,122(38):9058~9064.
[43] A S Gruber,D Zim,G Ebeling et al. Org. Lett.,2000,2(9):1287~1290
[44] D Zim,A S Gruber,G Ebeling et al. Org. Lett.,2000,2(18):2881~2884.
[45] X Gai,R Grigg,M I Ramzan et al. Chem. Commun.,2000,(20):2053~2054.
[46] S Darses,G Michaud,J P Genet. Eur. J. Org. Chem.,1999,(8):1875~1883.
[47] M S Viciu,R A III Kelly,E D Stevens et al. Org. Lett.,2003,5(9):1479~1482.
[48] G D Frey,J Schütz,E Herdtweck et al. Organometallics,2005,24(18):4416~4426.
[49] O Navarro,N Marion,Y Oonishi et al. J. Org. Chem.,2006,71(2):685~692.
[50] L Jin,W Wei,N Sun et al. Org. Chem. Front.,2018,5(16):2484~2491.
[51] J Broggi,H Clavier,S P Nolan. Organometallics,2008,27(21):5525~5531.
[52] B Alexandre,R Maxime,M Alami et al. ACS Catal.,2015,5(2):1386~1396.
[53] N Marion,S P Nolan. Acc. Chem. Res.,2008,41(11):1440~1449.
[54] R Navarro,E P Urriolabeitia,C Cativiela et al. J. Mol. Catal.A,1996,105(3):111~116.
[55] M A Stark,G Jones,C J Richards. Organometallics,2000,19(7):1282~1291.