RHODIUM-CATALYZED CARBON-CARBON BOND FORMATION

被引:1
作者
MATSUDA, I
机构
关键词
CARBON CARBON BOND FORMATION; RHODIUM CATALYST; RHODIUM CARBENOID; 4+2] CYCLOCOUPLING; ALDOL TYPE COUPLING; MICHAEL TYPE COUPLING; HYDROFORMYLATION; SILYLFORMYLATION; CYCLOCARBONYLATION;
D O I
10.5059/yukigoseikyokaishi.52.800
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Recent aspect of rhodium-catalyzed reactions is briefly surveyed from the view point of the carbon-carbon bond formation which is attained under almost neutral conditions. Topics focused here are carbene transfer, [4 +2] cyclocoupling, aldol and Michael type coupling, and carbonylations in which a certain type of rhodium complex behaves efficiently. A unique character of rhodium is demonstrated in the field of incorporation of CO, especially silylformylation which is accomplished by a combined use of triorganosilane, CO, and a rhodium complex in the presence of acetylenic compounds, aldehydes, or epoxides, alpha-Silylmethylene-beta-lactones and lactams are readily derived from the corresponding propargyl alcohol and propargylamine, respectively, under analogous procedure in the presence of a small amount of DBU. Bicyclo [3.3.0] octenone frameworks are also constructed by cyclocarbonylation of 1,6-diyne derivatives.
引用
收藏
页码:800 / 808
页数:9
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共 62 条
[21]   RHODIUM-CATALYZED CARBONYLATION OF ACETYLENES UNDER WATER-GAS SHIFT REACTION CONDITIONS - SELECTIVE SYNTHESIS OF FURAN-2(5H)-ONES [J].
JOH, T ;
DOYAMA, K ;
ONITSUKA, K ;
SHIOHARA, T ;
TAKAHASHI, S .
ORGANOMETALLICS, 1991, 10 (07) :2493-2498
[22]   NOVEL CYCLIZATION REACTIONS ON TRANSITION-METAL TEMPLATES - THE CATALYSIS OF INTRAMOLECULAR [4 + 2] CYCLOADDITIONS BY LOW VALENT RHODIUM COMPLEXES [J].
JOLLY, RS ;
LUEDTKE, G ;
SHEEHAN, D ;
LIVINGHOUSE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4965-4966
[23]   REGIOSELECTIVE HYDROCARBOXYLATIONS OF OLEFINIC AMINES - CHARACTERIZATION OF A KEY INTERMEDIATE [J].
KRAFFT, ME ;
WILSON, LJ ;
ONAN, KD .
TETRAHEDRON LETTERS, 1988, 29 (49) :6421-6424
[24]   TRANSITION-METAL-CATALYZED C-C BOND FORMATION VIA C-H ACTIVATION - INTERMOLECULAR HYDROACYLATION - THE ADDITION OF ALDEHYDES TO ALKENES [J].
MARDER, TB ;
ROE, DC ;
MILSTEIN, D .
ORGANOMETALLICS, 1988, 7 (06) :1451-1453
[25]   READY ACCESS TO ALPHA-(TRIORGANOSILYL)METHYLENE BETA-LACTONES BY MEANS OF RHODIUM-CATALYZED CYCLOCARBONYLATION OF SUBSTITUTED PROPARGYL ALCOHOLS [J].
MATSUDA, I ;
OGISO, A ;
SATO, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) :6120-6121
[26]   RHODIUM CATALYZED TRANSFORMATION OF PROPARGYLAMINES TO 2-SILYLMETHYL-2-ALKENALS - FORMAL SILYLFORMYLATION OF ALLENES [J].
MATSUDA, I ;
SAKAKIBARA, J ;
INOUE, H ;
NAGASHIMA, H .
TETRAHEDRON LETTERS, 1992, 33 (39) :5799-5802
[27]   AN EFFICIENT SILYLFORMYLATION OF ALKYNES CATALYZED BY RH4(CO)12 [J].
MATSUDA, I ;
OGISO, A ;
SATO, S ;
IZUMI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) :2332-2333
[28]   RHODIUM CATALYZED DIRECT COUPLING OF ALPHA,BETA-UNSATURATED KETONE, ALDEHYDE, AND TRIALKYLSILANE - AN EASY ACCESS TO REGIO-DEFINED ALDOL DERIVATIVES [J].
MATSUDA, I ;
TAKAHASHI, K ;
SATO, S .
TETRAHEDRON LETTERS, 1990, 31 (37) :5331-5334
[29]   A NOVEL-APPROACH TO ALPHA-SILYLMETHYLENE-BETA-LACTAMS VIA RH-CATALYZED SILYLCARBONYLATION OF PROPARGYLAMINE DERIVATIVES [J].
MATSUDA, I ;
SAKAKIBARA, J ;
NAGASHIMA, H .
TETRAHEDRON LETTERS, 1991, 32 (50) :7431-7434
[30]   CYCLO-CODIMERIZATION OF 1,3-BUTADIENE DERIVATIVES WITH NONACTIVATED TERMINAL ACETYLENES CATALYZED BY CATIONIC RHODIUM(I) COMPLEX [J].
MATSUDA, I ;
SHIBATA, M ;
SATO, S ;
IZUMI, Y .
TETRAHEDRON LETTERS, 1987, 28 (29) :3361-3362