Consecutive cross-coupling of o-phenylenedizinc compound with acyl and/or aryl halides in the presence of Pd(0)-tris(2,4,6-trimethoxyphenyl)phosphine

被引:11
作者
Saiga, A [1 ]
Hossain, KM [1 ]
Takagi, K [1 ]
机构
[1] Okayama Univ, Fac Sci, Dept Chem, Okayama 7008530, Japan
关键词
coupling reactions; palladium and compounds; polyaryls; zinc and compounds;
D O I
10.1016/S0040-4039(00)00679-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Consecutive cross-coupling of an o-phenylenedizine compound 1 with two different acyl or aryl halides or acyl and aryl halides was accomplished in one pot by the catalysis of Pd(0)-tris(2,4,6-trimethoxyphenyl)phosphine to yield a variety of functionalized unsymmetrical 1,2-disubstituted benzenes in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4629 / 4632
页数:4
相关论文
共 18 条
[1]   Synthesis of o-arylenedizinc compounds from 1-iodo-2-trifluoromethylsulfonyloxybenzenes and zinc powder and their synthetic application [J].
Amano, M ;
Saiga, A ;
Ikegami, R ;
Ogata, T ;
Takagi, K .
TETRAHEDRON LETTERS, 1998, 39 (47) :8667-8668
[2]   Highly regioselective palladium-catalyzed condensation of terminal acetylenes with 2,5-diiodobenzoic acid [J].
Balavoine, F ;
Madec, D ;
Mioskowski, C .
TETRAHEDRON LETTERS, 1999, 40 (48) :8351-8354
[3]   Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners [J].
Banwell, MG ;
Flynn, BL ;
Hamel, E ;
Hockless, DCR .
CHEMICAL COMMUNICATIONS, 1997, (02) :207-208
[4]   A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes [J].
Bowles, DM ;
Anthony, JE .
ORGANIC LETTERS, 2000, 2 (01) :85-87
[5]   Orthogonally protected dialkynes [J].
Ernst, A ;
Gobbi, L ;
Vasella, A .
TETRAHEDRON LETTERS, 1996, 37 (44) :7959-7962
[6]   A combined zirconocene benzyne-palladium cross-coupling route to substituted biphenyls and terphenyls [J].
Frid, M ;
Pérez, D ;
Peat, AJ ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9469-9470
[7]   Synthesis and structure of ortho-phenylenezinc [J].
Goedheijt, MS ;
Nijbacker, T ;
Akkerman, OS ;
Bickelhaupt, F ;
Veldman, N ;
Spek, AL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1550-1552
[8]   Synthesis of 4-alkyl-3,5-dibromo-, 3-bromo-4,5-dialkyl- and 3,4,5-trialkylpyridines via sequential metalation and metal-halogen exchange of 3,5-dibromopyridine [J].
Gu, YG ;
Bayburt, EK .
TETRAHEDRON LETTERS, 1996, 37 (15) :2565-2568
[9]   Versatile synthetic route to and DSC analysis of dehydrobenzoannulenes: Crystal structure of a heretofore inaccessible [20]annulene derivative [J].
Haley, MM ;
Bell, ML ;
English, JJ ;
Johnson, CA ;
Weakley, TJR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) :2956-2957
[10]   Preparation and coupling reaction of thienylmanganese bromides [J].
Kim, SH ;
Rieke, RD .
TETRAHEDRON LETTERS, 1997, 38 (06) :993-996