Generation of aryl radicals from arylboronic acids by manganese(III) acetate:: Synthesis of biaryls and heterobiaryls

被引:120
作者
Demir, AS [1 ]
Reis, Ö [1 ]
Emrullahoglu, M [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
关键词
D O I
10.1021/jo026466c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields are better than those from similar, previously described methods. Arylboronic acids carrying sensitive functional groups also work efficiently.
引用
收藏
页码:578 / 580
页数:3
相关论文
共 34 条
[1]   NEW METHODS OF FORMATION OF META-SUBSTITUTED AROMATIC-COMPOUNDS [J].
ADAMS, J ;
BELLEY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) :3878-3881
[2]  
AKIHIRO O, 1990, HETEROCYCLES, V31, P1951
[3]  
Bachmann W. E., 1944, ORG REACTIONS, V2, P224
[4]  
BEADLE JR, 1984, J ORG CHEM, V49, P1596
[5]   THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].
BRINGMANN, G ;
WALTER, R ;
WEIRICH, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991
[6]   OXIDATION REACTIONS OF MANGANESE(3) ACETATE .2. FORMATION OF GAMMA-LACTONES FROM OLEFINS AND ACETIC ACID [J].
BUSH, JB ;
FINKBEIN.H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (21) :5903-&
[7]   Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with furan and thiophene:: a novel method for hetero biaryl coupling [J].
Demir, AS ;
Reis, Ö ;
Emrullahoglu, M .
TETRAHEDRON, 2002, 58 (40) :8055-8058
[8]   Manganese(III) acetate-mediated oxidative coupling of phenylhydrazines with benzene:: a novel method for biaryl coupling [J].
Demir, AS ;
Reis, Ö ;
Özgül-Karaaslan, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :3042-3045
[9]   MANGANESE(III)-MEDIATED GAMMA-LACTONE ANNULATION [J].
FRISTAD, WE ;
PETERSON, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (01) :10-18
[10]   MANGANESE(III)-MEDIATED SPIRODILACTONIZATION [J].
FRISTAD, WE ;
HERSHBERGER, SS .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) :1026-1031