Scope and limitation of the nickel-catalyzed coupling reaction between lithium borates and mesylates

被引:35
作者
Kobayashi, Y [1 ]
William, AD [1 ]
Mizojiri, R [1 ]
机构
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
biaryl; borate; coupling; mesylate; nickel-catalyst;
D O I
10.1016/S0022-328X(02)01174-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Coupling reaction of aryl borates and mesylates derived from phenols and enols was studied. Mesylates with an electron-withdrawing group or ring were highly reactive at room temperature in the presence of NiCl2(PPh3)(2) to furnish the coupling products in good yields. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:91 / 97
页数:7
相关论文
共 63 条
[1]  
ARCADI A, 1990, SYNLETT, P47
[2]   PHENYLPROPIOLIC ACIDS .6. THE CYCLISATION OF DISSIMILARLY SUBSTITUTED PHENYLPROPIOLIC ANHYDRIDES TO THE CORRESPONDING 1-PHENYLNAPHTHALENES [J].
BADDAR, FG ;
ELASSAL, LS ;
DOSS, NA .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAR) :1027-1032
[4]   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
[5]   PALLADIUM-CATALYZED REDUCTION OF ARYL SULFONATES - REDUCTION VERSUS HYDROLYSIS AND SELECTIVITY CONTROL [J].
CABRI, W ;
DEBERNARDINIS, S ;
FRANCALANCI, F ;
PENCO, S ;
SANTI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :350-353
[6]  
Diederich F., 1997, METAL CATALYZED CROS
[7]   CONVERSION OF ALPHA,BETA-UNSATURATED ESTERS TO THEIR BETA,GAMMA-UNSATURATED ISOMERS BY PHOTOCHEMICAL DECONJUGATION [J].
DUHAIME, RM ;
LOMBARDO, DA ;
SKINNER, IA ;
WEEDON, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :873-879
[8]   THE DISCOVERY OF DUP-753, A POTENT, ORALLY ACTIVE NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONIST [J].
DUNCIA, JV ;
CARINI, DJ ;
CHIU, AT ;
JOHNSON, AL ;
PRICE, WA ;
WONG, PC ;
WEXLER, RR ;
TIMMERMANS, PBMWM .
MEDICINAL RESEARCH REVIEWS, 1992, 12 (02) :149-191
[9]   PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486
[10]   CATALYST TAILORING FOR PALLADIUM-MEDIATED CROSS COUPLING OF ARYLSTANNANES WITH VINYL TRIFLATES [J].
FARINA, V ;
ROTH, GP .
TETRAHEDRON LETTERS, 1991, 32 (34) :4243-4246