Regioselectivity in the Stille coupling reactions of 3,5-dibromo-2-pyrone

被引：71

作者：

Kim, WS ^{[1
]}

Kim, HJ ^{[1
]}

Cho, CG ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem, Seoul 133791, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 47期

关键词：

D O I：

10.1021/ja037043a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Stille couplings of 3,5-dibromo-2-pyrone normally take place regioselectively at C3, lower in electron density than C5, thus oxidative addition proceeds faster . When the reactions are carried out with Cu(I) in DMF or other polar aprotic solvent, however, the couplings occur predominantly at C5. The observed regiochemical reversal is attributed to the preferred formation of 5-pallado-2-pyrone intermediate which, in addition, turned out to be more reactive than 3-pallado-2-pyrone intermediate. Copyright © 2003 American Chemical Society.

引用

收藏

页码：14288 / 14289

页数：2

相关论文

共 24 条

[1] Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature [J].

Allred, GD ;

Liebeskind, LS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2748-2749

[2] Mechanism of the Stille reaction catalyzed by palladium ligated to arsine ligand:: PhPdl(AsPh3)(DMF) is the species reacting with vinylstannane in DMF [J].

Amatore, C ;

Bahsoun, AA ;

Jutand, A ;

Meyer, G ;

Ntepe, AN ;

Ricard, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4212-4222

[3]

[Anonymous], METAL CATALYZED CROS

[4] Use of the Stille coupling reaction on heteroaromatic cations:: Synthesis of substituted quinolizinium salts [J].

Barchín, BM ;

Valenciano, J ;

Cuadro, AM ;

Alvarez-Builla, J ;

Vaquero, JJ .

ORGANIC LETTERS, 1999, 1 (04) :545-547

[5] Mechanism of the Stille reaction.: 1.: The transmetalation step.: Coupling of R1I and R2SnBu3 catalyzed by trans-[PdR1IL2] (R1 = C6Cl2F3; R2 = vinyl, 4-methoxyphenyl; L = AsPh3) [J].

Casado, AL ;

Espinet, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :8978-8985

[6] Thermodynamics and mechanism of the reversible tin-to-palladium transmetalation of the furyl group [J].

Cotter, WD ;

Barbour, L ;

McNamara, KL ;

Hechter, R ;

Lachicotte, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :11016-11017

[7] TIN-COPPER TRANSMETALATION - CROSS-COUPLING OF ALPHA-HETEROATOM-SUBSTITUTED ALKYLTRIBUTYLSTANNANES WITH ORGANOHALIDES [J].

FALCK, JR ;

BHATT, RK ;

YE, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5973-5982

[8] ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].

FARINA, V ;

KAPADIA, S ;

KRISHNAN, B ;

WANG, CJ ;

LIEBESKIND, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911

[9]

Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01

[10]

FARINA V, 1996, ADV MET ORG, V5, P1