Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions

被引:6
作者
Mohammadiannejad, Kazem [1 ]
Hosseini, Raziyeh [2 ]
Ranjbar-Karimi, Reza [2 ]
机构
[1] Vali E Asr Univ Rafsanjan, Fac Sci, NMR Lab, Rafsanjan 77176, Iran
[2] Vali E Asr Univ Rafsanjan, Fac Sci, Dept Chem, Rafsanjan 77176, Iran
关键词
Triarylmethanes; C-C bond formation; Palladium catalysis; Suzuki-Miyaura cross-coupling reactions; Heck-type reactions; AROMATIC-ALDEHYDES; DERIVATIVES; HALIDES; ARENES;
D O I
10.5802/crchim.34
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel class of triarylmethanes (TRAMs) containing one or two biaryl moieties was synthesized efficiently through the Pd(PPh3)(4)-catalyzed Suzuki-Miyaura cross-coupling reaction of brominated TRAMs with arylboronic acid derivatives. We also demonstrate that brominated TRAMs can be efficiently functionalized via a one-pot, two-step Pd-catalyzed Heck-type process. This protocol provides convenient access to diverse vinylated TRAMs that are generally not obtained by using the common synthetic methods for TRAMs.
引用
收藏
页码:363 / 374
页数:12
相关论文
共 39 条
[1]   Synthesis of 2,3-diarylfluorenones by domino 'twofold Heck/electrocyclization/dehydrogenation' reactions of 2,3-dibromoindenone [J].
Akrawi, Omer A. ;
Khan, Afsar ;
Hussain, Munawar ;
Mohammed, Hamid H. ;
Villinger, Alexander ;
Langer, Peter .
TETRAHEDRON LETTERS, 2013, 54 (24) :3037-3039
[2]   Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds [J].
Albano, Gianluigi ;
Aronica, Laura Antonella .
CATALYSTS, 2020, 10 (01)
[3]   Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
NATURE PROTOCOLS, 2007, 2 (12) :3115-3121
[4]  
Biediger R. J., Patent, Patent No. [WO 2008/079371 A1., 2008079371]
[5]   Microwave-assisted aqueous Suzuki cross-coupling reactions [J].
Blettner, CG ;
König, WA ;
Stenzel, W ;
Schotten, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3885-3890
[6]   Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis [J].
Dobrounig, Patrick ;
Trobe, Melanie ;
Breinbauer, Rolf .
MONATSHEFTE FUR CHEMIE, 2017, 148 (01) :3-35
[7]   A Highly Efficient Pd(PPh3)4-Catalyzed Suzuki Cross-Coupling Method for the Preparation of 2-Nitrobiphenyls from 1-Chloro-2-nitrobenzenes and Phenylboronic Acids [J].
Elumalai, Vijayaragavan ;
Sandtorv, Alexander H. ;
Bjorsvik, Hans-Rene .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (07) :1344-1354
[8]   NEW TRIARYLMETHYL DERIVATIVES - BLOCK GROUPS - FOR ROTAXANES AND POLYROTAXANES [J].
GIBSON, HW ;
LEE, SH ;
ENGEN, PT ;
LECAVALIER, P ;
SZE, J ;
SHEN, YX ;
BHEDA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3748-3756
[9]   Bronsted- and Lewis acid-catalyzed cyclization giving rise to substituted anthracenes and acridines [J].
Goossens, R ;
Smet, M ;
Dehaen, W .
TETRAHEDRON LETTERS, 2002, 43 (37) :6605-6608
[10]   Multi-Component One-Pot Reaction of Aromatic Carbonyl Compounds, Tosylhydrazide, and Arylboronic Acids [J].
Gu, Ningning ;
Wei, Yu ;
Liu, Ping ;
Liu, Yan ;
Dai, Bin .
MOLECULES, 2017, 22 (12)