Palladium-pincer complex catalyzed C-C coupling of allyl nitriles with tosyl imines via regioselective allylic C-H bond functionalization

被引:60
作者
Aydin, Juhanes [1 ]
Szabo, Kalman J. [1 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
关键词
D O I
10.1021/ol801070n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mechanistically new palladium-pincer complex catalyzed allylation of sulfonimines is presented. This reaction involves C-H bond functionalization of allyl nitriles under mild conditions. The reaction proceeds with a high regioselectivity, without allyl rearrangement of the product. Modeling studies indicate that the carbon-carbon bond formation process proceeds via (eta(1)-allyl)palladium pincer complex intermediates.
引用
收藏
页码:2881 / 2884
页数:4
相关论文
共 48 条
[11]   PALLADIUM-CATALYZED ALLYLIC OXIDATION OF CYCLOHEXENES USING MOLECULAR-OXYGEN AS OXIDANT [J].
BYSTROM, SE ;
LARSSON, EM ;
AKERMARK, B .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5674-5675
[12]   Serial ligand catalysis: A highly selective allylic C-H oxidation [J].
Chen, MS ;
Prabagaran, N ;
Labenz, NA ;
White, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6970-6971
[13]   Sequential hydrocarbon functionalization: Allylic C-H oxidation/vinylic C-H arylation [J].
Delcamp, Jared H. ;
White, M. Christina .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) :15076-15077
[14]   Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds [J].
Dick, AR ;
Sanford, MS .
TETRAHEDRON, 2006, 62 (11) :2439-2463
[15]   Asymmetric addition of allylic nucleophiles to imino compounds [J].
Ding, H ;
Friestad, GK .
SYNTHESIS-STUTTGART, 2005, (17) :2815-2829
[16]  
Dupont J, 2001, EUR J INORG CHEM, P1917
[17]   REACTIONS OF CYCLOPALLADATED COMPOUNDS .21. VARIOUS EXAMPLES OF SULFUR-ASSISTED INTRAMOLECULAR PALLADATION OF ARYL AND ALKYL-GROUPS [J].
DUPONT, J ;
BEYDOUN, N ;
PFEFFER, M .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1989, (09) :1715-1720
[18]  
DUPONT J, 2005, EUR J INORG CHEM, V105, P2527
[19]  
DYKER G, 2005, HDN C H TRANSFORMATI
[20]   Chiral bis-π-allylpalladium complex catalyzed asymmetric allylation of imines:: Enhancement of the enantioselectivity and chemical yield in the presence of water [J].
Fernandes, RA ;
Stimac, A ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) :14133-14139