Catalytic C-H bond functionalization: Synthesis of arylsilanes by dehydrogenative transfer coupling of arenes and triethylsilane

被引：118

作者：

Ezbiansky, K

Djurovich, PI

LaForest, M

Sinning, DJ

Zayes, R

Berry, DH ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

[2] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA

来源：

ORGANOMETALLICS | 1998年 / 17卷 / 08期

关键词：

D O I：

10.1021/om980037g

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new catalytic route for the formation of arene-silicon bonds based on the transfer dehydrogenative coupling of triethylsilane with an arene (Ar-X: X = -CF3, -F, -H, -CH3, -Cl, -Br) in the presence of 3,3-dimethylbut-1-ene (Bu-t-ethylene) is reported. Rhodium and ruthenium catalysts (eta(5)-C5Me5)Rh(H)(2)(SiEt3)(2) and (eta(6)-arene)Ru(H)(2)(SiEt3)(2) and their corresponding dimeric chloride precursors not only catalyze the coupling of Et3SiH with an arene but additionally promote the dimerization of Et3SiH producing a carbosilane, Et3Si-CHMe-SiEt2H.

引用

收藏

页码：1455 / 1457

页数：3

相关论文

共 24 条

[1] COMPETITIVE GENERATION OF C-H AND C-SI BONDS BY REDUCTIVE ELIMINATION - FORMATION OF SILAMETALLACYCLES BY METALATION OF SILYL LIGANDS [J].

AIZENBERG, M ;

MILSTEIN, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (03) :317-319

[2]

Barry A. J., 1959, ACS MONOGR SER, V23, P246

[3] (ETA-6-HEXAMETHYLBENZENE)RUTHENIUM COMPLEXES [J].

BENNETT, MA ;

HUANG, TN ;

MATHESON, TW ;

SMITH, AK .

INORGANIC SYNTHESES, 1982, 21 :74-78

[4] TRIALKYLSILYL(HYDRIDO)(ETHYLENE)PENTAMETHYLCYCLOPENTADIENYLRHODIUM(III) COMPLEXES [J].

BENTZ, PO ;

RUIZ, J ;

MANN, BE ;

SPENCER, CM ;

MAITLIS, PM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) :1374-1375

[5] SELECTIVE H-D EXCHANGE IN ALKYLSILANES CATALYZED BY OSMIUM PHOSPHINE COMPLEXES - THE 1ST EVIDENCE FOR BETA-HYDROGEN ELIMINATION FROM A METAL SILYL [J].

BERRY, DH ;

PROCOPIO, LJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4099-4100

[6]

BERRY DH, 1996, Patent No. 5508460

[7] INSERTION OF ACETYLENES INTO CARBON HYDROGEN-BONDS CATALYZED BY RHODIUM TRIMETHYLPHOSPHINE COMPLEXES [J].

BOESE, WT ;

GOLDMAN, AS .

ORGANOMETALLICS, 1991, 10 (03) :782-786

[8] TRANSFER DEHYDROGENATIVE COUPLING OF TRIETHYLSILANE CATALYZED BY RUTHENIUM AND RHODIUM COMPLEXES - A NEW SI-C BOND-FORMING PROCESS [J].

DJUROVICH, PI ;

DOLICH, AR ;

BERRY, DH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (16) :1897-1898

[9] SYNTHESIS, STRUCTURE, AND C-H BOND ACTIVATION CHEMISTRY OF (ETA-6-ARENE)RU(H)2(SIME3)2 COMPLEXES [J].

DJUROVICH, PI ;

CARROLL, PJ ;

BERRY, DH .

ORGANOMETALLICS, 1994, 13 (07) :2551-2553

[10] SYNTHESIS, X-RAY, AND LOW-TEMPERATURE NEUTRON-DIFFRACTION STUDY OF A RHODIUM(V) COMPLEX - DIHYDRIDOBIS(TRIETHYLSILYL)-PENTAMETHYLCYCLOPENTADIENYLRHODIUM [J].

FERNANDEZ, MJ ;

BAILEY, PM ;

BENTZ, PO ;

RICCI, JS ;

KOETZLE, TF ;

MAITLIS, PM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5458-5463