Carbonylation of Ethene Catalysed by Pd(II)-Phosphine Complexes

被引:45
作者
Cavinato, Gianni [1 ]
Toniolo, Luigi [2 ]
机构
[1] Univ Padua, Dept Chem Sci, I-35131 Padua, Italy
[2] Ca Foscari Univ Venice, Dept Mol Sci & Nanosyst, I-30123 Venice, Italy
关键词
carbonylation; ethene; palladium-phosphine; catalysts; SUPPORTED PALLADIUM CATALYSTS; CO-ETHYLENE COPOLYMERIZATION; LOW-MOLECULAR-WEIGHT; X-RAY-STRUCTURE; MONOXIDE ALTERNATING COPOLYMER; AQUEOUS POLYKETONE LATICES; CARBOXYLIC-ACID ESTERS; SOLUBLE PD CATALYST; CARBON-MONOXIDE; CO/ETHENE COPOLYMERIZATION;
D O I
10.3390/molecules190915116
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This review deals with olefin carbonylation catalysed by Pd(II)-phosphine complexes in protic solvents. In particular, the results obtained in the carbonylation with ethene are reviewed. After a short description of the basic concepts relevant to this catalysis, the review treats in greater details the influence of the bite angle, skeletal rigidity, electronic and steric bulk properties of the ligand on the formation of the products, which range from high molecular weight perfectly alternating polyketones to methyl propanoate. It is shown that the steric bulk plays a major role in directing the selectivity. Particular emphasis is given to the factors governing the very active and selective catalysis to methyl propanoate, including the mechanism of the catalytic cycles with diphosphine- and monophosphine-catalysts. A brief note on the synthesis of methyl propanoate using a "Lucite" type catalyst in ionic liquids is also illustrated. A chapter is dedicated to the carbonylation of olefins in aqueous reaction media. The nonalternating CO-ethene copolymerization is also treated.
引用
收藏
页码:15116 / 15161
页数:46
相关论文
共 156 条
[11]   Reversibility of palladium-alkyl intermediate formation in deuterioalkoxycarbonylation of 1-hexene [J].
Benedek, C ;
Gömöry, A ;
Heil, B ;
Törös, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 622 (1-2) :112-120
[12]   NEW ALKOXYCARBONYL COMPLEXES OF PALLADIUM(II) AND THEIR ROLE IN CARBONYLATION REACTIONS CARRIED OUT IN THE PRESENCE OF AN ALKANOL [J].
BERTANI, R ;
CAVINATO, G ;
TONIOLO, L ;
VASAPOLLO, G .
JOURNAL OF MOLECULAR CATALYSIS, 1993, 84 (02) :165-176
[13]   Ligand effects in the non-alternating CO-ethylene copolymerization by palladium(II) catalysis [J].
Bettucci, Lorenzo ;
Bianchini, Claudio ;
Claver, Carmen ;
Suarez, Eduardo J. Garcia ;
Ruiz, Aurora ;
Meli, Andrea ;
Oberhauser, Werner .
DALTON TRANSACTIONS, 2007, 47 (47) :5590-5602
[14]   Ethylene carbonylation in methanol and in aqueous media by palladium(II) catalysts modified with 1,1'-bis(dialkylphosphino)ferrocenes [J].
Bianchini, C ;
Meli, A ;
Oberhauser, W ;
Parisel, S ;
Passaglia, E ;
Ciardelli, F ;
Gusev, OV ;
Kal'sin, AM ;
Vologdin, NV .
ORGANOMETALLICS, 2005, 24 (05) :1018-1030
[15]   Catalyst design and mechanistic aspects of the alternating copolymerisation of ethene and carbon monoxide by diphosphine-modified palladium catalysis [J].
Bianchini, C ;
Meli, A ;
Oberhauser, W .
DALTON TRANSACTIONS, 2003, (13) :2627-2635
[16]   Methoxycarbonylation of ethene by palladium(II) complexes with 1,1′-bis(diphenylphosphino)ferrocene (dppf) and 1,1′-bis(diphenylphosphino)octamethylferrocene (dppomf) [J].
Bianchini, C ;
Meli, A ;
Oberhauser, W ;
van Leeuwen, PWNM ;
Zuideveld, MA ;
Freixa, Z ;
Kamer, PCJ ;
Spek, AL ;
Gusev, OV ;
Kal'sin, AM .
ORGANOMETALLICS, 2003, 22 (12) :2409-2421
[17]   Studies of ligand and solvent effects in the alternating copolymerization of carbon monoxide and ethene by palladium-diphosphine catalysis [J].
Bianchini, C ;
Meli, A ;
Müller, G ;
Oberhauser, W ;
Passaglia, E .
ORGANOMETALLICS, 2002, 21 (23) :4965-4977
[18]   Alternating copolymerization of carbon monoxide and olefins by single-site metal catalysis [J].
Bianchini, C ;
Meli, A .
COORDINATION CHEMISTRY REVIEWS, 2002, 225 (1-2) :35-66
[19]   Ligand and solvent effects in the alternating copolymerization of carbon monoxide and olefins by palladium-diphosphine catalysis [J].
Bianchini, C ;
Lee, HM ;
Meli, A ;
Oberhauser, W ;
Peruzzini, M ;
Vizza, F .
ORGANOMETALLICS, 2002, 21 (01) :16-33
[20]   Copolymerization of carbon monoxide with ethene catalyzed by palladium(II) complexes of 1,3-bis(diphenylphosphino)propane ligands bearing different substituents on the carbon backbone [J].
Bianchini, C ;
Lee, HM ;
Meli, A ;
Moneti, S ;
Vizza, F ;
Fontani, M ;
Zanello, P .
MACROMOLECULES, 1999, 32 (13) :4183-4193