Cyclometallation of Heterocycles: A Reliable Strategy for Selective Functionalization

被引:25
作者
Cuesta, Luciano [1 ]
Urriolabeitia, Esteban P. [1 ]
机构
[1] Univ Zaragoza, CSIC, Inst Sintesis Quim & Catalisis Homogenea, E-50009 Zaragoza, Spain
关键词
chelation-assisted functionalization; cyclometallation; directing group; functionalization; heterocycle; metallacycle; palladium; regioselectivity; rhodium; ruthenium; C-H BOND; CATALYZED DIRECT ARYLATION; HETEROARENE CARBOXYLIC-ACIDS; N-H; CRYSTAL-STRUCTURE; HETEROAROMATIC-COMPOUNDS; PLATINUM COMPLEXES; PHOTOPHYSICAL PROPERTIES; RUTHENIUM(II) COMPLEXES; NITROGEN-HETEROCYCLES;
D O I
10.1080/02603594.2012.700971
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Heterocyclic compounds are of paramount importance in essentially all fields of chemistry and in our daily life. Therefore, the synthesis and modification of such compounds is a constantly expanding field in synthetic chemistry. Recent developments of functionalization of heterocycles by means of cyclometallation (also called chelation-assisted functionalization), both stoichiometric and catalytic, indicate that this strategy displays enormous potential. In particular, this method facilitates considerably the synthesis of functionalized heterocycles in a regioselective (site-selective) manner, and also provides novel types of synthetic transformations.
引用
收藏
页码:55 / 85
页数:31
相关论文
共 195 条
[81]   Ester-Directed Regioselective Borylation of Heteroarenes Catalyzed by a Silica-Supported Iridium Complex [J].
Kawamorita, Soichiro ;
Ohmiya, Hirohisa ;
Sawamura, Masaya .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (11) :3855-3858
[82]   NOVEL TYPE OF METALATION REACTION - CYCLOMETALLATION OF HETEROCYCLIC AMINES BY DICYCLOPENTADIENYLMETHYLTITANIUM [J].
KLEI, B ;
TEUBEN, JH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (15) :659-660
[83]   Terpyridine-analogous (N,N,C)-tridentate ligands: Synthesis, structures, and electrochemical properties of ruthenium(II) complexes bearing tridentate pyridinium and pyridinylidene ligands [J].
Koizumi, T ;
Tomon, T ;
Tanaka, K .
ORGANOMETALLICS, 2003, 22 (05) :970-975
[84]   Synthesis of Cyclometallated Platinum Complexes with Substituted Thienylpyridines and Detailed Characterization of Their Luminescence Properties [J].
Kozhevnikov, Dmitry N. ;
Kozhevnikov, Valery N. ;
Ustinova, Maria M. ;
Santoro, Amedeo ;
Bruce, Duncan W. ;
Koenig, Burkhard ;
Czerwieniec, Rafal ;
Fischer, Tobias ;
Zabel, Manfred ;
Yersin, Hartmut .
INORGANIC CHEMISTRY, 2009, 48 (09) :4179-4189
[85]   Luminescent Organoplatinum(II) Complexes with Functionalized Cyclometalated C∧N∧C Ligands: Structures, Photophysical Properties, and Material Applications [J].
Kui, Steven C. F. ;
Hung, Faan-Fung ;
Lai, Shiu-Lun ;
Yuen, Mai-Yan ;
Kwok, Chi-Chung ;
Low, Kam-Hung ;
Chui, Stephen Sin-Yin ;
Che, Chi-Ming .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (01) :96-109
[86]   Hydroarylation of acetylenes, acrylates, and isocyanates with heteroaromatic compounds under rhenium catalysis [J].
Kuninobu, Yoichiro ;
Kikuchi, Kou ;
Tokunaga, Yukimi ;
Nishina, Yuta ;
Takai, Kazuhiko .
TETRAHEDRON, 2008, 64 (26) :5974-5981
[87]   Kinetic and Theoretical Comprehension of Diverse Rate Laws and Reactivity Gaps in Coriolus hirsutus Laccase-Catalyzed Oxidation of Acido and Cyclometalated RuII Complexes [J].
Kurzeev, Sergey A. ;
Vilesov, Alexander S. ;
Fedorova, Tatyana V. ;
Stepanova, Elena V. ;
Koroleva, Olga V. ;
Bukh, Christian ;
Bjerrum, Morten J. ;
Kurnikov, Igor V. ;
Ryabov, Alexander D. .
BIOCHEMISTRY, 2009, 48 (21) :4519-4527
[88]   OXIDATIVE ADDITION OF N-H BONDS TO IRIDIUM - SYNTHESIS AND STRUCTURE OF (HETEROCYCLIC AMINE)IRIDIUM HYDRIDE COMPLEXES [J].
LADIPO, FT ;
MEROLA, JS .
INORGANIC CHEMISTRY, 1990, 29 (21) :4172-4173
[89]   High-yielding palladium-catalyzed intramolecular alkane arylation: Reaction development and mechanistic studies [J].
Lafrance, Marc ;
Gorelsky, Serge I. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) :14570-+
[90]   Direct palladium-catalyzed ortho-arylation of benzylamines [J].
Lazareva, Anna ;
Daugulis, Olafs .
ORGANIC LETTERS, 2006, 8 (23) :5211-5213