Palladium-catalysed Grignard cross-coupling using highly concentrated Grignards in methyl-tetrahydrofuran

被引:27
作者
Milton, Edward J. [1 ]
Clarke, Matthew L. [1 ]
机构
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews, Fife, Scotland
基金
英国工程与自然科学研究理事会;
关键词
ARYL CHLORIDES; ALKYL-HALIDES; REAGENTS; COMPLEXES; ETHERS;
D O I
10.1039/b921026a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cross-coupling of Grignard reagents at 5 molar concentration in methyl-tetrahydrofuran with no added reaction solvents can be achieved with the appropriate matching of catalyst to substrate, significantly reducing solvent use when compared to a typical protocol in tetrahydrofuran. Me-THF was also used in an improved microwave accelerated synthesis of the [Pd(L)Cl-2] pre-catalysts from sodium tetrachloropalladate in very high yield.
引用
收藏
页码:381 / 383
页数:3
相关论文
共 25 条
[1]   Use of "homeopathic" ligand-free palladium as catalyst for aryl-aryl coupling reactions [J].
Alimardanov, A ;
de Vondervoort, LSV ;
de Vries, AHM ;
de Vries, JG .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1812-1817
[2]   Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions [J].
Aycock, David F. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) :156-159
[3]   Palladium-Catalysed C-C Coupling: Then and Now [J].
Barnard, Chris .
PLATINUM METALS REVIEW, 2008, 52 (01) :38-45
[4]   Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents [J].
Bedford, RB ;
Betham, M ;
Bruce, DW ;
Davis, SA ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2006, (13) :1398-1400
[5]   Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2005, (33) :4161-4163
[6]  
BOYLES AL, 1998, TETRAHEDRON LETT, V39, P7766
[7]   1,1'-BIS[(ALKYL/ARYL)PHOSPHINO]FERROCENES - SYNTHESIS AND METAL-COMPLEX FORMATION - CRYSTAL-STRUCTURE OF 3 METAL-COMPLEXES OF FE(ETA-5-C5H4PPH2)2- [J].
BUTLER, IR ;
CULLEN, WR ;
KIM, TJ ;
RETTIG, SJ ;
TROTTER, J .
ORGANOMETALLICS, 1985, 4 (06) :972-980
[8]   A convenient catalyst system for microwave accelerated cross-coupling of a range of aryl boronic acids with aryl chlorides [J].
Clarke, Matthew L. ;
France, Marcia B. ;
Fuentes, Jose A. ;
Milton, Edward J. ;
Roff, Geoffrey J. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2007, 3
[9]   The importance of ligand steric effects on transmetalation [J].
Clarke, ML ;
Heydt, M .
ORGANOMETALLICS, 2005, 24 (26) :6475-6478
[10]   First microwave-accelerated hiyama coupling of aryl- and vinylsiloxane derivatives: Clean cross-coupling of aryl chlorides within minutes [J].
Clarke, ML .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :303-307