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
[1]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[2]   Dabbling with air-stable organoaluminum species [J].
Biswas, K ;
Chapron, A ;
Cooper, T ;
Fraser, PK ;
Novak, A ;
Prieto, O ;
Woodward, S .
PURE AND APPLIED CHEMISTRY, 2006, 78 (02) :511-518
[3]   Palladium-catalyzed methylation of aryl and vinyl halides by stabilized methylaluminum and methylgallium complexes [J].
Blum, J ;
Gelman, D ;
Baidossi, W ;
Shakh, E ;
Rosenfeld, A ;
Aizenshtat, Z ;
Wassermann, BC ;
Frick, M ;
Heymer, B ;
Schutte, S ;
Wernik, S ;
Schumann, H .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8681-8686
[4]   Hydrophobic, highly conductive ambient-temperature molten salts [J].
Bonhote, P ;
Dias, AP ;
Papageorgiou, N ;
Kalyanasundaram, K ;
Gratzel, M .
INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178
[5]   INTERACTIONS OF 1,4-DIAZABICYCLO[2.2.2]OCTANE WITH GROUP-III METAL TRIMETHYLS - STRUCTURES OF ME3M.N(C2H4)3N.MME3 (M = AL, GA) [J].
BRADFORD, AM ;
BRADLEY, DC ;
HURSTHOUSE, MB ;
MOTEVALLI, M .
ORGANOMETALLICS, 1992, 11 (01) :111-115
[6]   User-friendly methylation of aryl and vinyl halides and pseudohalides with DABAL-Me3 [J].
Cooper, T ;
Novak, A ;
Humphreys, LD ;
Walker, MD ;
Woodward, S .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (06) :686-690
[7]   The polymerization of some derivatives of trimethylaluminum [J].
Davidson, N ;
Brown, HC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :316-324
[8]   On the noninnocent nature of 1,3-dialkylimidazolium ionic liquids [J].
Dupont, J ;
Spencer, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (40) :5296-5297
[9]  
Dyson P.J., 2005, METAL CATALYSED REAC
[10]   Decolorization of ionic liquids for spectroscopy [J].
Earle, Martyn J. ;
Gordon, Charles M. ;
Plechkova, Natalia V. ;
Seddon, Kenneth R. ;
Welton, Thomas .
ANALYTICAL CHEMISTRY, 2007, 79 (02) :758-764