4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane: a superior 2-carbon building block for vinylboronate Heck couplings

被引：39

作者：

Lightfoot, AP

Maw, G

Thirsk, C

Twiddle, SJR

Whiting, A

机构：

[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England

[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

[3] Pfizer Ltd, Global Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 41期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2003.08.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane is a superior reagent in terms of stability and reactivity in comparison to the vinylboronate pinacol ester, giving improved selectivity for Heck versus Suzuki coupling with both aryl iodides and bromides, and being easier to prepare and store. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7645 / 7648

页数：4

相关论文

共 18 条

[1] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[2] Proximity, photochemical reactivity, and intermolecular H-1-C-13 cross polarization in benzophenone-d(10) and cyclohexane in the zeolite NaX [J].

Cizmeciyan, D ;

Sonnichsen, LB ;

GarciaGaribay, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (01) :184-188

[3]

Crisp GT, 1998, CHEM SOC REV, V27, P427

[4] ADDITION OF ARYL HALIDES TO TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) [J].

FITTON, P ;

RICK, EA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (02) :287-&

[5] VIRIDENOMYCIN - NEW ANTIBIOTIC [J].

HASEGAWA, T ;

KAMIYA, T ;

HENMI, T ;

IWASAKI, H ;

YAMATODANI, S .

JOURNAL OF ANTIBIOTICS, 1975, 28 (03) :167-175

[6] PALLADIUM-CATALYZED VINYLIC HYDROGEN SUBSTITUTION REACTIONS WITH ARYL, BENZYL, AND STYRYL HALIDES [J].

HECK, RF ;

NOLLEY, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) :2320-&

[7] Highly stereoselective palladium catalysed cross-coupling approaches to the total synthesis of phthoxazolin A [J].

Hénaff, N ;

Whiting, A .

TETRAHEDRON, 2000, 56 (29) :5193-5204

[8] A convergent stereoselective total synthesis of racemic phthoxazolin A [J].

Hénaff, N ;

Whiting, A .

ORGANIC LETTERS, 1999, 1 (07) :1137-1139

[9] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .23. TRANSFER OF CHIRALITY ON ADDITION OF (ALPHA-CHLOROALLYL)BORONATES TO ALDEHYDES [J].

HOFFMANN, RW ;

LANDMANN, B .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (06) :2013-2024

[10] HECK VERSUS SUZUKI PALLADIUM-CATALYZED CROSS-COUPLING OF A VINYLBORONATE ESTER WITH ARYL HALIDES [J].

HUNT, AR ;

STEWART, SK ;

WHITING, A .

TETRAHEDRON LETTERS, 1993, 34 (22) :3599-3602