Serial ligand catalysis: A highly selective allylic C-H oxidation

被引:367
作者
Chen, MS [1 ]
Prabagaran, N [1 ]
Labenz, NA [1 ]
White, MC [1 ]
机构
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ja0500198
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We are reporting a mild, chemo-, and highly regioselective Pd(II)-catalyzed allylic oxidation of α-olefins to furnish branched allylic esters that proceeds via a novel serial ligand catalysis mechanism in which two different ligands (i.e., vinyl sulfoxide 2 and BQ) interact sequentially with the metal to promote distinct steps of the catalytic cycle (i.e., C-H cleavage and π-allyl functionalization, respectively). Copyright © 2005 American Chemical Society.
引用
收藏
页码:6970 / 6971
页数:2
相关论文
共 23 条
[1]   AMINATION OF PI-ALLYLPALLADIUM CHLORIDE COMPLEXES - A MECHANISTIC STUDY [J].
AKERMARK, B ;
AKERMARK, G ;
HEGEDUS, LS ;
ZETTERBERG, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3037-3040
[2]  
[Anonymous], 1979, TETRAHEDRON LETT
[3]   EVIDENCE FOR (PI-ALLYL)PALLADIUM(II)(QUINONE) COMPLEXES IN THE PALLADIUM-CATALYZED 1,4-DIACETOXYLATION OF CONJUGATED DIENES [J].
BACKVALL, JE ;
GOGOLL, A .
TETRAHEDRON LETTERS, 1988, 29 (18) :2243-2246
[4]  
BACKVALL JE, 1984, J ORG CHEM, V49, P4619
[5]   A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation [J].
Chen, MS ;
White, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) :1346-1347
[6]   Hydrocarbon oxidation vs C-C bond-forming approaches for efficient syntheses of oxygenated molecules [J].
Fraunhoffer, KJ ;
Bachovchin, DA ;
White, MC .
ORGANIC LETTERS, 2005, 7 (02) :223-226
[7]   Ni(II)-catalyzed cross-coupling between polyfunctional arylzinc derivatives and primary alkyl iodides [J].
Giovannini, R ;
Knochel, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (43) :11186-11187
[8]   USE OF SULFOXIDES AS COCATALYSTS IN THE PALLADIUM QUINONE-CATALYZED 1,4-DIACETOXYLATION OF 1,3-DIENES - AN EXAMPLE OF LIGAND-ACCELERATED CATALYSIS [J].
GRENNBERG, H ;
GOGOLL, A ;
BACKVALL, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5808-5811
[9]   PREPARATION OF ALLYLIC ACETATES FROM SIMPLE ALKENES BY PALLADIUM(II)-CATALYZED ACETOXYLATION [J].
HANSSON, S ;
HEUMANN, A ;
REIN, T ;
AKERMARK, B .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :975-984
[10]   First enantioselective alkylations of monosubstituted allylic acetates catalyzed by chiral iridium complexes [J].
Janssen, JP ;
Helmchen, G .
TETRAHEDRON LETTERS, 1997, 38 (46) :8025-8026