Manganese(III) acetate-mediated synthesis of biaryls under microwave irradiation

被引:29
作者
Demir, Ayhan S. [1 ]
Findik, Hamide [1 ]
Saygili, Nezire [2 ]
Subasi, N. Tuna [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
[2] Hacettepe Univ, Fac Pharm, TR-06100 Ankara, Turkey
关键词
CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; SOLVENT-FREE; PALLADIUM COMPLEXES; HIGHLY EFFICIENT; ARYL CHLORIDES; CATALYSTS; PHENYLHYDRAZINES; CHEMISTRY; REAGENT;
D O I
10.1016/j.tet.2009.12.018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Manganese(Ill) acetate (Mn(OAc)(3))-mediated synthesis of biaryls and heterobiaryls starting from arylboronic acid was developed under microwave irradiation in high yields Microwaves were also used for the synthesis of Mn(OAc)(3) from KMnO4 and acetic acid Additional irradiation of this in situ generated Mn(OAc)3 with arylboronic acids, which in turn furnished the biaryls in high yields In a one pot reaction This IS superior from the point of view of yield, short reaction time, sensitive functional group toleration, and more environmentally friendly than the reported methods with a minimum amount of benzene and thiophene as a reagent but not as a solvent (C) 2009 Elsevier Ltd All rights reserved
引用
收藏
页码:1308 / 1312
页数:5
相关论文
共 48 条
[1]   An Overview of Syntheses of Apogalanthamine Analogues and 7-Aza Derivatives of Steganacin and Steganone [J].
Appukkuttan, Prasad ;
Van der Eycken, Erik .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (35) :5867-5886
[2]   Clean and efficient microwave-solvent-free conversion of homochiral amines, α-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives [J].
Aydogan, F ;
Demir, AS .
TETRAHEDRON, 2005, 61 (12) :3019-3023
[3]   New and clean synthesis of N-substituted pyrroles under microwave irradiation [J].
Aydogan, Feray ;
Basarir, Mehmet ;
Yolacan, Cigdem ;
Demir, Ayhan S. .
TETRAHEDRON, 2007, 63 (39) :9746-9750
[4]   Palladium Supported on a Polyionic Resin as an Efficient, Ligand-Free, and Recyclable Catalyst for Heck, Suzuki-Miyaura, and Sonogashira Reactions [J].
Basu, Basudeb ;
Das, Sajal ;
Das, Pralay ;
Mandal, Bablee ;
Banerjee, Dipanjan ;
Almqvist, Fredrik .
SYNTHESIS-STUTTGART, 2009, (07) :1137-1146
[5]   Reaction of aryl di-, tri-, or tetrabromides with arylboronic acids or alkenes in the presence of a palladium-tetraphosphine catalyst [J].
Berthiol, F ;
Kondolff, I ;
Doucet, H ;
Santelli, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (17) :2786-2798
[6]   MICROWAVE-ASSISTED ORGANIC-REACTIONS [J].
CADDICK, S .
TETRAHEDRON, 1995, 51 (38) :10403-10432
[7]   Hydrophilic CNC-pincer palladium complexes:: A source for highly efficient, recyclable homogeneous catalysts in Suzuki-Miyaura cross-coupling [J].
Churruca, Fatima ;
SanMartin, Raul ;
Ines, Blanca ;
Tellitu, Imanol ;
Dominguez, Esther .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1836-1840
[8]   New pyridine ONN-pincer gold and palladium complexes: Synthesis, characterization and catalysis in hydrogenation, hydrosilylation and C-C cross-coupling reactions [J].
Debono, N. ;
Iglesias, M. ;
Sanchez, F. .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (16) :2470-2476
[9]  
DEKLEIN WJ, 1986, ORGANIC SYNTHESES OX
[10]   Role of copper species in the oxidative dimerization of arylboronic acids:: Synthesis of symmetrical biaryls [J].
Demir, AS ;
Reis, Ö ;
Emrullahoglu, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10130-10134