Highly stereoselective hydrocarbation of terminal alkynes via Pt-catalyzed hydrosilylation/Pd-catalyzed cross-coupling reactions

被引：122

作者：

Denmark, SE ^{[1
]}

Wang, ZG ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 07期

关键词：

D O I：

10.1021/ol0156751

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling, The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates, Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.

引用

页码：1073 / 1076

页数：4

共 48 条

[1] A straightforward route to polyenylsilanes by palladium- or nickel-catalyzed cross-coupling reactions [J].

Babudri, F ;

Farinola, GM ;

Fiandanese, V ;

Mazzone, L ;

Naso, F .

TETRAHEDRON, 1998, 54 (07) :1085-1094

[2] Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes [J].

Boden, CDJ ;

Pattenden, G ;

Ye, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20) :2417-2419

[3] The synthesis of novel amino acids via hydroboration-Suzuki cross coupling [J].

Campbell, AD ;

Raynham, TM ;

Taylor, RJK .

TETRAHEDRON LETTERS, 1999, 40 (28) :5263-5266

[4] A CONVENIENT AND NOVEL ROUTE TO BIS(ETA-ALKYNE)PLATINUM(0) AND OTHER PLATINUM(0) COMPLEXES FROM SPEIER HYDROSILYLATION CATALYST H2[PTCL6].XH2O - X-RAY STRUCTURE OF [PT((ETA-CH2=CHSIME2)2O)(P-TERT-BU3)] [J].

CHANDRA, G ;

LO, PY ;

HITCHCOCK, PB ;

LAPPERT, MF .

ORGANOMETALLICS, 1987, 6 (01) :191-192

[5] Highly stereospecific, palladium-catalyzed cross-coupling of alkenylsilanols [J].

Denmark, SE ;

Wehrli, D .

ORGANIC LETTERS, 2000, 2 (04) :565-568

[6] Synthesis of unsymmetrical biaryls from arylsilacyclobutanes [J].

Denmark, SE ;

Wu, ZC .

ORGANIC LETTERS, 1999, 1 (09) :1495-1498

[7] Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes [J].

Denmark, SE ;

Choi, JY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5821-5822

[8]

Denmark SE, 2000, SYNTHESIS-STUTTGART, P999

[9] Convergence of mechanistic pathways in the palladium(0)-catalyzed cross-coupling of alkenylsilacyclobutanes and alkenylsilanols [J].

Denmark, SE ;

Wehrli, D ;

Choi, JY .

ORGANIC LETTERS, 2000, 2 (16) :2491-2494

[10] Mild and general cross-coupling of (α-alkoxyvinyl)silanols and -silyl hydrides [J].

Denmark, SE ;

Neuville, L .

ORGANIC LETTERS, 2000, 2 (20) :3221-3224

← 1 2 3 4 5 →