Rhodium-catalyzed selective C-H functionalization of NNN tridentate chelating compounds via a rollover pathway

被引:29
作者
Hong, Seung Youn [1 ,2 ]
Kwak, Jaesung [1 ,2 ]
Chang, Sukbok [1 ,2 ]
机构
[1] Korea Adv Inst Sci & Technol, Dept Chem, Daejeon 305701, South Korea
[2] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Daejeon 305701, South Korea
关键词
TERPYRIDINE COMPLEXES; DIRECT ARYLATION; VINYL ARENES; CYCLOMETALATION; LIGANDS; HYDROARYLATION; HYDROBORATION; REACTIVITY; CHEMISTRY; OLEFINS;
D O I
10.1039/c5cc09960a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reported herein is the first example of the Rh(NHC)-catalyzed selective bis C-H alkylation of NNN tridentate chelating compounds in reaction with alkenes. The observed excellent site-selectivity can readily be explained by the postulated rollover pathway in the C-H bond activation step. The reaction is highly facile affording bis-alkylated tridentate products in high yields over a broad range of versatile heteroarene substrates and alkene reactants including ethylene gas, thus enabling its applications to be feasible in coordination and synthetic chemistry.
引用
收藏
页码:3159 / 3162
页数:4
相关论文
共 53 条
[1]   Pyrazole-Based PCN Pincer Complexes of Palladium(II): Mono- and Dinuclear Hydroxide Complexes and Ligand Rollover C-H Activation [J].
Bailey, Wilson D. ;
Luconi, Lapo ;
Rossin, Andrea ;
Yakhvarov, Dmitry ;
Flowers, Sarah E. ;
Kaminsky, Werner ;
Kemp, Richard A. ;
Giambastiani, Giuliano ;
Goldberg, Karen I. .
ORGANOMETALLICS, 2015, 34 (16) :3998-4010
[2]  
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[3]   "Rollover" cyclometalation - early history, recent developments, mechanistic insights and application aspects [J].
Butschke, Burkhard ;
Schwarz, Helmut .
CHEMICAL SCIENCE, 2012, 3 (02) :308-326
[4]   Roll-over Cyclometalation of 2,2′-Bipyridine Platinum(II) Complexes in the Gas Phase: A Combined Experimental and Computational Study [J].
Butschke, Burkhard ;
Schlangen, Maria ;
Schroeder, Detlef ;
Schwarz, Helmut .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) :11050-11060
[5]   Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].
Campbell, Michael G. ;
Ritter, Tobias .
CHEMICAL REVIEWS, 2015, 115 (02) :612-633
[6]   Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].
Campeau, LC ;
Fagnou, K .
CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264
[7]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[8]   Iron- and Cobalt-Catalyzed Alkene Hydrogenation: Catalysis with Both Redox-Active and Strong Field Ligands [J].
Chirik, Paul J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (06) :1687-1695
[9]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[10]   LIGAND REACTIVITY IN POLYPYRIDINE COMPLEXES - THE DEUTERIATION OF THE BIS(2,2'-6',2''-TERPYRIDINE)RUTHENIUM(II) CATION [J].
CONSTABLE, EC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (12) :2687-2689