Palladium-Catalyzed Diarylmethyl C(sp3)-C(sp2) Bond Formation: A New Coupling Approach toward Triarylmethanes

被引:87
作者
Xia, Ying [1 ,2 ]
Hu, Fangdong [3 ]
Liu, Zhenxing [1 ,2 ]
Qu, Peiyuan [1 ,2 ]
Ge, Rui [1 ,2 ]
Ma, Chen [3 ]
Zhang, Yan [1 ,2 ]
Wang, Jianbo [1 ,2 ]
机构
[1] Peking Univ, BNLMS, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
[3] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
关键词
ARYL HALIDES; MIGRATORY INSERTION; N-TOSYLHYDRAZONES; SUBSTITUTED OLEFINS; NOBEL LECTURE; ARYLATION; DERIVATIVES; REACTIVITY; COMPLEXES; CARBENE;
D O I
10.1021/ol400690t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed reductive coupling reactions between N-tosylhydrazones and aryl halides lead to the formation of C(sp(3))-C(sp(2)) bonds. This approach provides a general route for the synthesis of triarylmethanes.
引用
收藏
页码:1784 / 1787
页数:4
相关论文
共 52 条
[1]   Triaryl methane derivatives as antiproliferative agents [J].
Al-Qawasmeh, RA ;
Lee, Y ;
Cao, MY ;
Gu, XP ;
Vassilakos, A ;
Wright, JA ;
Young, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) :347-350
[2]   Formation of a vinyliminium palladium complex by C-C coupling in vinylcarbene palladium aryl complexes [J].
Albéniz, AC ;
Espinet, P ;
Pérez-Mateo, A ;
Nova, A ;
Ujaque, G .
ORGANOMETALLICS, 2006, 25 (05) :1293-1297
[3]  
Albéniz AC, 2002, ANGEW CHEM INT EDIT, V41, P2363, DOI 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO
[4]  
2-9
[5]   N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins [J].
Barluenga, José ;
Moriel, Patricia ;
Valdes, Carlos ;
Aznar, Fernando .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5587-5590
[6]   Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].
Barluenga, Jose ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500
[7]   Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides [J].
Barluenga, Jose ;
Escribano, Maria ;
Aznar, Fernando ;
Valdes, Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) :6856-6859
[8]   Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds in diarylmethanes [J].
Bellomo, Ana ;
Zhang, Jiadi ;
Trongsiriwat, Nisalak ;
Walsh, Patrick J. .
CHEMICAL SCIENCE, 2013, 4 (02) :849-857
[9]   Pd-Catalyzed Reaction of Sterically Hindered Hydrazones with Aryl Halides: Synthesis of Tetra-Substituted Olefins Related to iso-Combretastatin A4 [J].
Brachet, Etienne ;
Hamze, Abdallah ;
Peyrat, Jean-Francois ;
Brion, Jean-Daniel ;
Alami, Mouad .
ORGANIC LETTERS, 2010, 12 (18) :4042-4045
[10]   The first PdII complex of a non-heteroatom stabilised carbene ligand [J].
Bröring, M ;
Brandt, CD ;
Stellwag, S .
CHEMICAL COMMUNICATIONS, 2003, (18) :2344-2345