Nickel-Catalyzed Selective Conversion of Two Different Aldehydes to Cross-Coupled Esters

被引:95
作者
Hoshimoto, Yoichi [1 ]
Ohashi, Masato [1 ,2 ]
Ogoshi, Sensuke [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Ctr Atom & Mol Technol, Suita, Osaka 5650871, Japan
关键词
TISHCHENKO REACTION; BOND FORMATION; HYDROACYLATION; DIMERIZATION; COMPLEXES; DECARBONYLATION; MECHANISM; KETONES; ALKYNES;
D O I
10.1021/ja109908x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of a Ni(0)/NHC catalyst, an equimolar mixture of aliphatic and aryl aldehydes can be employed to selectively yield a single cross-coupled ester. This reaction can be applied to a variety of aliphatic (1 degrees, 2 degrees, cyc-2 degrees, and 3 degrees) and aryl aldehyde combinations. The reaction represents 100% atom efficiency and generates no waste. Mechanistic studies have revealed that the striking feature of the reaction is the simultaneous coordination of two aldehydes to Ni(0).
引用
收藏
页码:4668 / 4671
页数:4
相关论文
共 41 条
[1]   Structure of an η1 nickel O-enolate:: Mechanistic implications in catalytic enyne cyclizations [J].
Amarasinghe, KKD ;
Chowdhury, SK ;
Heeg, MJ ;
Montgomery, J .
ORGANOMETALLICS, 2001, 20 (03) :370-372
[2]   Organoactinides promote the Tishchenko reaction: The myth of inactive actinide-alkoxo complexes [J].
Andrea, Tamer ;
Barnea, Eyal ;
Eisen, Moris S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2454-2455
[3]  
Anslyn E.V., 2006, MODERN PHYS ORGANIC, P421
[4]   Reactions of a hexahydride-osmium complex with aldehydes:: Double C-Hα activation-decarbonylation and single C-Hα activation-hydroxylation tandem processes and catalytic Tishchenko reactions [J].
Barrio, P ;
Esteruelas, MA ;
Oñate, E .
ORGANOMETALLICS, 2004, 23 (06) :1340-1348
[5]   Dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes [J].
Baxter, Ryan D. ;
Montgomery, John .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (30) :9662-+
[6]   HOMOGENEOUS CATALYSIS - CATALYTIC INTRAMOLECULAR CONVERSION OF 1,4-DIALDEHYDES TO GAMMA-LACTONES [J].
BERGENS, SH ;
FAIRLIE, DP ;
BOSNICH, B .
ORGANOMETALLICS, 1990, 9 (03) :566-571
[7]   EVIDENCE FOR C-O BOND FORMATION, ALDEHYDE DECARBONYLATION, AND DIMERIZATION BY REACTION OF FORMALDEHYDE AND ACETALDEHYDE WITH TRANS-ROIR(CO)(PPH3)2 [J].
BERNARD, KA ;
ATWOOD, JD .
ORGANOMETALLICS, 1988, 7 (01) :235-236
[8]   REACTIONS OF LOW-VALENT METAL COMPLEXES WITH FLUOROCARBONS .17. TERTIARY-ARSINE-NICKEL COMPLEXES [J].
BROWNING, J ;
GREEN, M ;
STONE, FGA .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1971, (03) :453-&
[9]   Modification of mesoporous silicate SBA-15 with tris[bis(trimethylsilyl)amido]samarium and its utility in Tishchenko reaction [J].
Chen, YH ;
Zhu, ZY ;
Zhang, J ;
Shen, JZ ;
Zhou, XG .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (16) :3783-3789
[10]   Tunable Bromomagnesium Thiolate Tishchenko Reaction Catalysts: Intermolecular Aldehyde-Trifluoromethylketone Coupling [J].
Cronin, Linda ;
Manoni, Francesco ;
O'Connor, Cornelius J. ;
Connon, Stephen J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (17) :3045-3048