Synthesis of arylacetic acid derivatives from diethyl malonate using in situ formed palladium(1,3-dialkylimidazolidin-2-ylidene) catalysts

被引:19
作者
Özdemir, I
Yigit, M
Çetinkaya, E
Çetinkaya, B
机构
[1] Ege Univ, Dept Chem, TR-35100 Izmir, Turkey
[2] Inonu Univ, Dept Chem, TR-44069 Malatya, Turkey
关键词
arylations; palladium catalysts; NHC complexes; diethyl malonate;
D O I
10.1016/j.tetlet.2004.06.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The in situ prepared three component system Pd(OAc)(2)/1,3-bis(alkyl) imidazolinium halide LHX (1-5)/Cs2CO3 catalyses the arylation of diethyl malonate efficiently with accompanying dealkoxycarbonylation. Imidazolinium salts with bulky benzyl and alkoxyethyl groups were found to be the most efficient and afforded alpha-arylacetates in high yields when employing a wide variety of substrates. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5823 / 5825
页数:3
相关论文
共 29 条
[11]   Efficient synthesis of α-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates [J].
Jorgensen, M ;
Lee, S ;
Liu, XX ;
Wolkowski, JP ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (42) :12557-12565
[12]   Palladium catalyzed arylation of malonate accompanying in situ dealkoxcarbonylation [J].
Kondo, Y ;
Inamoto, K ;
Uchiyama, M ;
Sakamoto, T .
CHEMICAL COMMUNICATIONS, 2001, (24) :2704-2705
[13]   Palladium-catalyzed α-arylation of esters and protected amino acids [J].
Lee, S ;
Beare, NA ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) :8410-8411
[14]  
Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
[15]  
2-U
[16]  
Lloyd-Jones GC, 2002, ANGEW CHEM INT EDIT, V41, P953, DOI 10.1002/1521-3773(20020315)41:6<953::AID-ANIE953>3.0.CO
[17]  
2-9
[18]   Novel palladium imidazole catalysts for Suzuki cross-coupling reactions [J].
Mathews, CJ ;
Smith, PJ ;
Welton, T .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 206 (1-2) :77-82
[19]   Donor-functionalized heterocyclic carbene complexes of palladium(II): Efficient catalysts for C-C coupling reactions [J].
McGuinness, DS ;
Cavell, KJ .
ORGANOMETALLICS, 2000, 19 (05) :741-748
[20]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483