Complete control of the chemoselectivity in catalytic carbene transfer reactions from ethyl diazoacetate:: An N-heterocyclic carbene-Cu system that suppresses diazo coupling

被引:114
作者
Fructos, MR
Belderrain, TR
Nicasio, MC
Nolan, SP
Kaur, H
Díaz-Requejo, MM
Pérez, PJ
机构
[1] Univ Huelva, Dept Quim & Ciencia Mat, Huelva 21007, Spain
[2] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
关键词
D O I
10.1021/ja047284y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The complex IPrCuCl (1) catalyzes the transfer of the :CHCO2Et group from ethyl diazoacetate (EDA) to unsaturated and saturated substrates (olefins, amine, alcohols) with very high yields. In the absence of substrate, the complex 1 does not react with EDA to give the diazo coupling products (fumarate and maleate), a rare example in the field of metal-catalyzed diazocompounds decomposition. Copyright © 2003 American Chemical Society.
引用
收藏
页码:10846 / 10847
页数:2
相关论文
共 32 条
[1]   Chelated iridium(III) bis-carbene complexes as air-stable catalysts for transfer hydrogenation [J].
Albrecht, M ;
Miecznikowski, JR ;
Samuel, A ;
Faller, JW ;
Crabtree, RH .
ORGANOMETALLICS, 2002, 21 (17) :3596-3604
[2]   Looking for stable carbenes: The difficulty in starting anew [J].
Arduengo, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :913-921
[3]   Synthesis of iridium complexes with novel planar chiral chelating imidazolylidene ligands [J].
Bolm, C ;
Focken, T ;
Raabe, G .
TETRAHEDRON-ASYMMETRY, 2003, 14 (12) :1733-1746
[4]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[5]  
CENTINKAYA B, 1997, J ORGANOMET CHEM, V534, P153
[6]   First chelated chiral N-Heterocyclic bis-carbene complexes [J].
Clyne, DS ;
Jin, J ;
Genest, E ;
Gallucci, JC ;
RajanBabu, TV .
ORGANIC LETTERS, 2000, 2 (08) :1125-1128
[7]   Copper(I)-homoscorpionate catalysts for the preferential, kinetically controlled cis cyclopropanation of α-olefins with ethyl diazoacetate [J].
Díaz-Requejo, MM ;
Caballero, A ;
Belderraín, TR ;
Nicasio, MC ;
Trofimenko, S ;
Pérez, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :978-983
[8]   Unprecedented highly cis-diastereoselective olefin cyclopropanation using copper homoscorpionate catalysts [J].
Díaz-Requejo, MM ;
Belderraín, TR ;
Trofimenko, S ;
Pérez, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :3167-3168
[9]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[10]   Structural characterization and catalytic activity of the rhodium-carbene complex Rh(PPh3)2(IMes)Cl (IMes = bis(1,3-(2,4,6-trimethylphenyl)imidazol-2-ylidene) [J].
Grasa, GA ;
Moore, Z ;
Martin, KL ;
Stevens, ED ;
Nolan, SP ;
Paquet, V ;
Lebel, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 658 (1-2) :126-131