Highly selective coupling of alkenes and aldehydes catalyzed by [Ni(NHC){P(OPh)3}]:: Synergy between a strong σ donor and a strong π acceptor

被引:103
作者
Ho, Chun-Yu [1 ]
Jamison, Timothy F. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1002/anie.200603907
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Give and take: Both a strong electron donor (1) and a strong electron acceptor (P(OPh)3) are necessary for a highly selective, nickel-catalyzed coupling reaction between alkenes, aldehydes, and silyl triflates (see scheme; cod = cycloocta-1,5-diene, Tf=trifluoromethanesulfonyl). This synergistic effect may also be useful in other transformations catalyzed by NHC-metal complexes (NHC = N-heterocyclic carbene). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:782 / 785
页数:4
相关论文
共 45 条
[11]  
Giovannini R, 1998, ANGEW CHEM INT EDIT, V37, P2387, DOI 10.1002/(SICI)1521-3773(19980918)37:17<2387::AID-ANIE2387>3.0.CO
[12]  
2-M
[13]   New efficient nickel-catalyzed cross-coupling reaction between two Csp3 centers [J].
Giovannini, R ;
Stüdemann, T ;
Devasagayaraj, A ;
Dussin, G ;
Knochel, P .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3544-3553
[14]  
Giovannini R., 1998, ANGEW CHEM-GER EDIT, V110, P2512
[15]  
Herrmann W. A., 2002, ANGEW CHEM, V114, P1342, DOI [DOI 10.1002/1521-3757(20020415)114:8<1342::AID-ANGE1342>3.0.CO
[16]  
2-A, DOI 10.1016/j.ccr.2014.12.019]
[17]  
Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
[18]  
2-Y
[19]   Nickel-catalyzed, carbonyl-ene-type reactions: Selective for alpha olefins and more efficient with electron-rich aldehydes [J].
Ho, CY ;
Ng, SS ;
Jamison, TF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (16) :5362-5363
[20]   Highly efficient nickel-catalyzed heck reaction using Ni(acac)2/N-heterocyclic carbene catalyst [J].
Inamoto, K ;
Kuroda, J ;
Danjo, T ;
Sakamoto, T .
SYNLETT, 2005, (10) :1624-1626