NICKEL-CATALYZED SUBSTITUTIONS OF ARYL TERT-BUTYL SULFONES WITH ORGANOMETALLIC REAGENTS - SYNTHESIS OF ORTHO-SUBSTITUTED UNSYMMETRICAL BIARYLS

被引:46
作者
CLAYDEN, J [1 ]
COONEY, JJA [1 ]
JULIA, M [1 ]
机构
[1] ECOLE NORMALE SUPER,CHIM LAB,F-75231 PARIS 05,FRANCE
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 01期
关键词
D O I
10.1039/p19950000007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of a catalytic amount of a nickel salt, aryl tert-butyl sulfones react with aryl Grignard reagents to give biaryls. This reaction is used in conjunction with the powerful ortho-lithiation-directing ability of aryl tert-butyl sulfonyl groups to make-unsymmetrical ortho-substituted biaryls. In certain cases, the substitution of an aryl alkylsulfonyl group by an organometallic reagent is possible without a Transition metal catalyst.
引用
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页码:7 / 14
页数:8
相关论文
共 103 条
[1]   THE HYDROALUMINATION OF OMEGA-TERBUTOXY ALKYNES - AN EASY ACCESS TO OMEGA-HYDROXY ALKENYL IODIDES - APPLICATION TO THE SYNTHESIS OF DIENIC INSECT PHEROMONES [J].
ALEXAKIS, A ;
DUFFAULT, JM .
TETRAHEDRON LETTERS, 1988, 29 (48) :6243-6246
[2]   MILD PROTECTION AND DEPROTECTION OF ALCOHOLS AS TERT-BUTYL ETHERS IN THE FIELD OF PHEROMONE SYNTHESIS [J].
ALEXAKIS, A ;
GARDETTE, M ;
COLIN, S .
TETRAHEDRON LETTERS, 1988, 29 (24) :2951-2954
[3]   SEQUENTIAL DIRECTED ORTHO METALATION BORONIC ACID CROSS-COUPLING REACTIONS - A GENERAL REGIOSPECIFIC ROUTE TO OXYGENATED DIBENZO[B,D]PYRAN-6-ONES RELATED TO ELLAGIC ACID [J].
ALO, BI ;
KANDIL, A ;
PATIL, PA ;
SHARP, MJ ;
SIDDIQUI, MA ;
SNIECKUS, V ;
JOSEPHY, PD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3763-3768
[4]   CYTOCHALASIN SUPPORT STUDIES .10. NUCLEOPHILIC AND ELECTROPHILIC MERCAPTANYLATIONS VIA 2-(TRIMETHYLSILYL)ETHANETHIOL-DERIVED REAGENTS [J].
ANDERSON, MB ;
RANASINGHE, MG ;
PALMER, JT ;
FUCHS, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (13) :3125-3127
[5]   ALKYL-OXYGEN FISSION IN CARBOXYLIC ESTERS .8. ESTERS OF PARA-METHYLTHIO-DIPHENYLCARBINOLS AND PARA-METHYLSULPHONYL-DIPHENYLCARBINOLS [J].
BALFE, MP ;
DABBY, RE ;
KENYON, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1951, (FEB) :382-385
[6]  
BONNER WA, 1966, CHEM ORGANIC SULPHUR, V2, P35
[7]   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
[8]  
BUTENKO GG, 1981, IAN SSSR KH, P2057
[9]   SYNTHETIC CONNECTIONS TO THE AROMATIC DIRECTED METALATION REACTION - ITERATIVE ORTHO METALATION-CROSS COUPLING TACTICS FOR THE CONSTRUCTION OF POLYPHENYLS [J].
CHENG, W ;
SNIECKUS, V .
TETRAHEDRON LETTERS, 1987, 28 (43) :5097-5098
[10]  
CHIANELLI D, 1982, SYNTHESIS-STUTTGART, P475