Palladium-catalyzed cross-coupling reactions of arylmetal compounds with beta-substituted alpha-iodoenones and a cyclohexyl triflate

被引：12

作者：

Bosse, F ^{[1
]}

Tunoori, AR ^{[1
]}

Niestroj, AJ ^{[1
]}

Gronwald, O ^{[1
]}

Maier, ME ^{[1
]}

机构：

[1] UNIV HALLE WITTENBERG,FACHBEREICH CHEM,INST ORGAN CHEM,D-06120 HALLE,GERMANY

来源：

TETRAHEDRON | 1996年 / 52卷 / 28期

关键词：

D O I：

10.1016/0040-4020(96)00489-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electron-rich arylstannanes were found to couple with alpha-iodoenones in the presence of Pd-2(dba)(3) CHCl3, a weak-coordinating ligand [AsPh(3) or Pd(o-tol)(3)] and CuI (0.75-1.0 equiv) to give sterically hindered alpha-arylcyclohexenones 15-20. In addition, compounds 19, 22 and 23 were prepared by Suzuki coupling reactions of the cyclohexyl derivatives 7c,f and 11, respectively, with the arylboronic acid 21. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9485 / 9498

页数：14

共 51 条

[1]

BARTON DHR, 1992, J CHEM SOC P1, V11, P1365

[2] INTRAMOLECULAR FACILITATION OF ARYL-TRANSFER FROM TIN IN PALLADIUM-CATALYZED CROSS-COUPLING [J].

BROWN, JM ;

PEARSON, M ;

JASTRZEBSKI, JTBH ;

VANKOTEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (19) :1440-1441

[3]

DATA JB, 1961, J MED CHEM, V4, P324

[4] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[5] AN IMPROVED SYNTHESIS OF ETHYL N-(METHOXYCARBONYL)-2,5-DIHYDRO-1H-PYRROLE-3-CARBOXYLATE [J].

DUPRE, B ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :3197-3198

[6] ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].

FARINA, V ;

KAPADIA, S ;

KRISHNAN, B ;

WANG, CJ ;

LIEBESKIND, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911

[7]

Herrmann W. A., 1995, ANGEW CHEM, V107, P1989

[8] PALLADACYCLES AS STRUCTURALLY DEFINED CATALYSTS FOR THE HECK OLEFINATION OF CHLOROARENES AND BROMOARENES [J].

HERRMANN, WA ;

BROSSMER, C ;

OFELE, K ;

REISINGER, CP ;

PRIERMEIER, T ;

BELLER, M ;

FISCHER, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1844-1848

[9] MODIFIED STILLE COUPLING UTILIZING ALPHA-IODOENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW .

TETRAHEDRON LETTERS, 1992, 33 (07) :919-922

[10] DIRECT ALPHA-IODINATION OF CYCLOALKENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW ;

WOVKULICH, PM ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1992, 33 (07) :917-918

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