Facile synthesis of steroidal phenyl ketones via homogeneous catalytic carbonylation

被引:34
作者
Skoda-Földes, R
Székvölgyi, Z
Kollár, L
Berente, Z
Horváth, J
Tuba, Z
机构
[1] Univ Veszprem, Hungarian Acad Sci, Dept Organ Chem, H-8200 Veszprem, Hungary
[2] Univ Veszprem, Res Grp Petrochem, H-8200 Veszprem, Hungary
[3] Janus Pannonius Univ, Dept Inorgan Chem, H-7624 Pecs, Hungary
[4] Hungarian Acad Sci, Res Grp Chem Sensors, H-7624 Pecs, Hungary
[5] Univ Pecs, Sch Med, Dept Biochem, H-7623 Pecs, Hungary
[6] Chem Works Gedeon Richter Ltd, Budapest, Hungary
基金
匈牙利科学研究基金会;
关键词
Pd-catalysis; carbonylation; phenyl ketones; steroids;
D O I
10.1016/S0040-4020(00)00241-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Steroidal phenyl ketones were synthesised in high yields by palladium-catalysed carbonylation reactions of 17-iodo-androst-16-ene derivatives in the presence of NaBPh4 under mild reaction conditions. Alkenyl bromides or enol triflates gave lower yields in the same reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3415 / 3418
页数:4
相关论文
共 18 条
[1]  
Alper H., 1979, TETRAHEDRON LETT, V20, P2665
[2]   BETA-ARYL AND BETA-VINYL-ALPHA,BETA-DIDEHYDRO-ALPHA-AMINOACID DERIVATIVES THROUGH THE PALLADIUM-CATALYZED REACTION OF ARYL AND VINYL TRIFLATES WITH METHYL ALPHA-ACETAMIDOACRYLATE [J].
ARCADI, A ;
CACCHI, S ;
MARINELLI, F ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON, 1990, 46 (20) :7151-7164
[3]  
CHO CS, 1993, J ORGANOMET CHEM, V443, P253
[4]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF VINYL AND ARYL TRIFLATES WITH TETRAARYLBORATES [J].
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1992, 33 (33) :4815-4818
[5]   SELECTIVE SYNTHESES OF ALIPHATIC KETONES USING SODIUM TETRACARBONYLFERRATE(-II) [J].
COLLMAN, JP ;
CLARK, DR ;
WINTER, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (05) :1788-&
[6]   PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1557-1565
[7]   Palladium catalysed cascade cyclisation-anion capture, relay switches and molecular queues [J].
Grigg, R ;
Sridharan, V .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :65-87
[8]   PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF ARYLFLUOROSILANES WITH ARYL IODIDES - A CONVENIENT SYNTHESIS OF DIARYL KETONES [J].
HATANAKA, Y ;
HIYAMA, T .
CHEMISTRY LETTERS, 1989, (11) :2049-2052
[9]   SYNTHESIS OF UNSYMMETRICAL BIARYL KETONES VIA PALLADIUM-CATALYZED CARBONYLATIVE CROSS-COUPLING REACTION OF ARYLBORONIC ACIDS WITH IODOARENES [J].
ISHIYAMA, T ;
KIZAKI, H ;
MIYAURA, N ;
SUZUKI, A .
TETRAHEDRON LETTERS, 1993, 34 (47) :7595-7598
[10]   CLEAVAGE OF C-N BONDS OF TERTIARY-AMINES AND CARBONYLATION OF ORGANIC HALIDES WITH PALLADIUM COMPLEXES AS CATALYSTS LEADING TO FORMATION OF TERTIARY AMIDES [J].
KOBAYASHI, T ;
TANAKA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 231 (01) :C12-C14