Transition-metal-catalyzed C-H functionalization of pyrazoles

被引:35
作者
Kang, Eunsu [1 ,2 ]
Kim, Hyun Tae [1 ,2 ]
Joo, Jung Min [1 ,2 ]
机构
[1] Pusan Natl Univ, Dept Chem, Busan 46241, South Korea
[2] Pusan Natl Univ, Chem Inst Funct Mat, Busan 46241, South Korea
关键词
DIRECT ARYLATION; UBIQUITOUS FUNCTIONALITY; GENERAL-APPROACH; HETEROARENES; ACTIVATION; ALKENYLATION; BORYLATION; REACTIVITY; AMINATION; ALKYNES;
D O I
10.1039/d0ob01265c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review describes recent advances in transition-metal-catalyzed C-H functionalization reactions of pyrazoles to form new C-C and C-heteroatom bonds on the pyrazole ring. In contrast to traditional cross-coupling reactions that require pre-functionalized pyrazoles, direct C-H functionalization reactions provide access to a wide range of functionalized pyrazoles in a single step. Various strategies are presented and the efficiency and regioselectivity are described with respect to the types of functional groups that are installed.
引用
收藏
页码:6192 / 6210
页数:19
相关论文
共 91 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]  
[Anonymous], 2008, SURG OBES RELAT DI S
[3]   Catalytic C-H Allylation and Benzylation of Pyrazoles [J].
Bae, Seri ;
Jang, Ha-Lim ;
Jung, Haeun ;
Joo, Jung Min .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) :690-697
[4]   Pd-Catalysed Direct 5-Arylation of 1-Methylpyrazole with Aryl Bromides [J].
Beladhria, Anissa ;
Beydoun, Kassem ;
Ben Ammar, Hamed ;
Ben Salem, Ridha ;
Doucet, Henri .
SYNTHESIS-STUTTGART, 2011, (16) :2553-2560
[5]   Mild Palladium-Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate [J].
Bellina, Fabio ;
Lessi, Marco ;
Manzini, Chiara .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) :5621-5630
[6]   Regioselectivity in palladium-catalysed direct arylation of 5-membered ring heteroaromatics [J].
Bheeter, Charles Beromeo ;
Chen, Lu ;
Soule, Jean-Francois ;
Doucet, Henri .
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (07) :2005-2049
[7]   A palladium-catalyzed alkylation/direct arylation synthesis of nitrogen-containing heterocycles [J].
Blaszykowski, Christophe ;
Aktoudianakis, Evangelos ;
Adberico, Dino ;
Bressy, Cyril ;
Hulcoop, David G. ;
Jafarpour, Farnaz ;
Joushaghani, Arash ;
Laleu, Benoit ;
Lautens, Mark .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1888-1897
[8]   Reactivity of 1-(2-bromobenzyl)-4-halopyrazoles in intermolecular and intramolecular Pd-catalysed direct arylations [J].
Brahim, Mariem ;
Ben Ammar, Hamed ;
Soule, Jean-Francois ;
Doucet, Henri .
TETRAHEDRON, 2016, 72 (29) :4312-4320
[9]   Conditions for palladium-catalyzed direct arylations of 4-bromo and 4-iodo N-substituted pyrazoles without C-Br or C-I bond cleavage [J].
Brahim, Mariem ;
Smari, Imen ;
Ben Ammar, Hamed ;
Ben Hassine, Bechir ;
Soule, Jean-Francois ;
Doucet, Henri .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (08) :917-926
[10]   Optimization of a pyrazoloquinolinone class of Chk1 kinase inhibitors [J].
Brnardic, Edward J. ;
Garbaccio, Robert M. ;
Fraley, Mark E. ;
Tasber, Edward S. ;
Steen, Justin T. ;
Arrington, Kenneth L. ;
Dudkin, Vadim Y. ;
Hartman, George D. ;
Stirdivant, Steven M. ;
Drakas, Bob A. ;
Rickert, Keith ;
Walsh, Eileen S. ;
Hamilton, Kelly ;
Buser, Carolyn A. ;
Hardwick, James ;
Tao, Weikang ;
Beek, Stephen C. ;
Mao, Xianzhi ;
Lobell, Robert B. ;
Sepp-Lorenzino, Laura ;
Yan, Youwei ;
Ikuta, Mari ;
Munshi, Sanjeev K. ;
Kuo, Lawrence C. ;
Kreatsoulas, Constantine .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (21) :5989-5994