Rare-Earth-Catalyzed C-H Bond Addition of Pyridines to Olefins

被引：214
作者：
Guan, Bing-Tao
Hou, Zhaomin [1 ]
机构：
[1] RIKEN Adv Sci Inst, Organometall Chem Lab, Wako, Saitama 3510198, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 45期
关键词：
STYRENE-STYRENE SEQUENCES; SYNDIOSPECIFIC COPOLYMERIZATION; SELECTIVE ALKENYLATION; AROMATIC HETEROCYCLES; INSERTION CHEMISTRY; ALKYNYL COMPLEXES; COUPLING REACTION; SCANDIUM; ACTIVATION; POLYMERIZATION;
D O I：
10.1021/ja208129t
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and general protocol for the ortho-alkylation of pyridines via C-H addition to olefins has been developed, using cationic half-sandwich rare-earth catalysts, which provides an atom-economical method for the synthesis of alkylated pyridine derivatives. A wide range of pyridine and olefin substrates including alpha-olefins, styrenes, and conjugated dienes are compatible with the catalysts.
引用
收藏
页码：18086 / 18089
页数：4
相关论文
共 73 条
[1]   Chiral Heterobidentate Pyridine Ligands for Asymmetric Catalysis [J].
Arena, Carmela G. ;
Arico, Girolamo .
CURRENT ORGANIC CHEMISTRY, 2010, 14 (06) :546-580
[2]   Formation of a dicationic yttrium η2-pyridyl complex from an yttrium methyl dication by C-H activation of pyridine [J].
Arndt, S ;
Elvidge, BR ;
Zeimentz, PM ;
Spaniol, TP ;
Okuda, J .
ORGANOMETALLICS, 2006, 25 (03) :793-795
[3]   The bohimann-rahtz pyridine synthesis: From discovery to applications [J].
Bagley, Mark C. ;
Glover, Christian ;
Merritt, Eleanor A. .
SYNLETT, 2007, (16) :2459-2482
[4]   Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].
Berman, Ashley M. ;
Lewis, Jared C. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+
[5]   A Direct, Copper-Catalyzed Functionalization of Pyridines with Alkynes [J].
Beveridge, Ramsay E. ;
Arndtsen, Bruce A. .
SYNTHESIS-STUTTGART, 2010, (06) :1000-1008
[6]   Olefin oligomerization, homopolymerization and copolymerization by late transition metals supported by (imino)pyridine ligands [J].
Bianchini, Claudio ;
Giambastiani, Giuliano ;
Luconi, Lapo ;
Meli, Andrea .
COORDINATION CHEMISTRY REVIEWS, 2010, 254 (5-6) :431-455
[7]   Ring-opening reactions of aromatic N-heterocycles by scandium and yttrium alkyl complexes [J].
Carver, Colin T. ;
Diaconescu, Paula L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) :7558-+
[8]   Steric and chelate directing effects in aromatic borylation [J].
Cho, JY ;
Iverson, CN ;
Smith, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12868-12869
[9]   Palladium-Catalyzed Minisci Reaction with Simple Alcohols [J].
Correia, Camille A. ;
Yang, Luo ;
Li, Chao-Jun .
ORGANIC LETTERS, 2011, 13 (17) :4581-4583
[10]   INSERTION CHEMISTRY OF CP-ASTERISK(2)Y(2-PYRIDYL) AND MOLECULAR-STRUCTURE OF THE UNEXPECTED CO INSERTION PRODUCT (CP-ASTERISK(2)Y)2(MU-ETA-2-ETA-2-OC(NC5H4)2) [J].
DEELMAN, BJ ;
STEVELS, WM ;
TEUBEN, JH ;
LAKIN, MT ;
SPEK, AL .
ORGANOMETALLICS, 1994, 13 (10) :3881-3891
12345678