Polyglycerol as a high-loading support for boronic acids with application in solution-phase Suzuki cross-couplings

被引：43

作者：

Hebel, A

Haag, R

机构：

[1] Univ Freiburg, Freiburger Mat Forschungszentrum, D-79104 Freiburg, Germany

[2] Univ Freiburg, Inst Makromol Chem, D-79104 Freiburg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 26期

关键词：

D O I：

10.1021/jo026076q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, we describe the usage of a soluble high-loading polyglycerol support for functionalized boronic acids without further linker design. The quantitatively formed polyglycerol boron esters were subsequently employed in homogeneous Suzuki cross-coupling reactions to give high yields (84-91%) of functional biaryls with minimal amounts of the Pd catalyst (0.2 mol %). In situ precipitation and ultrafiltration were used as simple and effective purification protocols. Furthermore, the reaction conditions were optimized by the choice of the solvent and the catalyst.

引用

收藏

页码：9452 / 9455

页数：4

相关论文

共 37 条

[1] Solid-phase synthesis of isoxazoles using vinyl ethers as chameleon catches [J].

Barrett, AGM ;

Procopiou, PA ;

Voigtmann, U .

ORGANIC LETTERS, 2001, 3 (20) :3165-3168

[2] The use of soluble polymers to effect homogeneous catalyst separation and reuse [J].

Bergbreiter, DE .

CATALYSIS TODAY, 1998, 42 (04) :389-397

[3]

Blettner CG, 1999, SYNLETT, P307

[4] Synthesis of tetrasubstituted ethylenes on solid support via resin capture [J].

Brown, SD ;

Armstrong, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) :6331-6332

[5] Diels-Alder reactions of chiral 1,3-dienes [J].

Crisp, GT ;

Gebauer, MG .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8425-8431

[6] Parallel synthesis of prostaglandin E1 analogues [J].

Dragoli, DR ;

Thompson, LA ;

O'Brien, J ;

Ellman, JA .

JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (06) :534-539

[7] Two new iodine-capped carbon rods [J].

Gao, K ;

Goroff, NS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9320-9321

[8] Universal solid-phase approach for the immobilization, derivatization, and resin-to-resin transfer reactions of boronic acids [J].

Gravel, M ;

Thompson, KA ;

Zak, M ;

Bérubé, C ;

Hall, DG .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :3-15

[9] Resin-to-resin Suzuki coupling of solid supported arylboronic acids [J].

Gravel, M ;

Bérubé, CD ;

Hall, DG .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (03) :228-231

[10] Solid-phase Suzuki coupling for C-C bond formation [J].

Guiles, JW ;

Johnson, SG ;

Murray, WV .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5169-5171

← 1 2 3 4 →