Palladium-catalysed methylation of aryl halides in ionic liquids with stabilized AlMe3

被引:9
作者
Conte, Valeria [1 ]
Fiorani, Giulia [1 ]
Floris, Barbara [1 ]
Galloni, Pierluca [1 ]
Woodward, Simon [2 ]
机构
[1] Univ Roma Tor Vergata, Dipartimento Sci & Tecnol Chim, I-00133 Rome, Italy
[2] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
基金
英国工程与自然科学研究理事会;
关键词
Methylation; Pd-catalysis; Ionic liquids; Cross-coupling reactions; Trialkylaluminum reagents; DABAL-Me-3; VINYL HALIDES; ORGANOALUMINUM;
D O I
10.1016/j.apcata.2010.04.005
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A new protocol for the methylation of aryl halides using the AlMe3 analogue DABAL-Me-3 in a VOC/IL biphasic system is described. Very good isolated yields and chemoselectivities (methylation vs homocoupling), were observed in alkylmethylimidazolium and DABCO-based ILs, in presence of a bulky substituted phosphine (XPhos) and the structurally related sulfonated phosphine (XPhosSO(3)H). Recycling experiments of the IL-catalyst systems were satisfactory only in case of the butyldimethylimidazolium IL due to catalyst loss to the VOC phase. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:161 / 168
页数:8
相关论文
共 24 条
[11]   Ionic liquids and catalysis: Recent progress from knowledge to applications [J].
Olivier-Bourbigou, H. ;
Magna, L. ;
Morvan, D. .
APPLIED CATALYSIS A-GENERAL, 2010, 373 (1-2) :1-56
[12]   Comparative kinetic investigations in ionic liquids using the MTO/peroxide system [J].
Owens, GS ;
Abu-Omar, MM .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 187 (02) :215-225
[13]   Catalysis in ionic liquids [J].
Parvulescu, Vasile I. ;
Hardacre, Christopher .
CHEMICAL REVIEWS, 2007, 107 (06) :2615-2665
[14]  
Perrin D.D., 1980, PURIFICATION LAB CHE, VSecond
[15]   Applications of ionic liquids in the chemical industry [J].
Plechkova, Natalia V. ;
Seddon, Kenneth R. .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (01) :123-150
[16]  
SCHLOSSER M, 1994, ORGANOMETALLICS SYNT, P448
[17]   Intramolecularly stabilized organoaluminium and organogallium compounds: Synthesis and X-ray crystal structures of some dimethylaluminium and -gallium alkoxides Me(2)M-O-R-OR' and amides Me(2)M-NH-R-OR' [J].
Schumann, H ;
Frick, M ;
Heymer, B ;
Girgsdies, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 512 (1-2) :117-126
[18]   Ionic liquids: A versatile medium for palladium-catalyzed reactions [J].
Singh, Ram ;
Sharma, Mukul ;
Mamgain, Ritu ;
Rawat, Diwan S. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2008, 19 (03) :357-379
[19]  
Sirieix J, 2000, SYNLETT, P1613
[20]  
TOMA S, COMMUNICATION