Fully Substituted Pyranones via Quasi-Heterogeneous Genuinely Ligand-Free Migita-Stille Coupling of lodoacrylates

被引：15

作者：

Kratochvil, Jiri ^{[1
]}

Novak, Zdenek ^{[1
]}

Ghavre, Mukund ^{[1
]}

Novakova, Lucie ^{[2
]}

Ruzicka, Ales ^{[3
]}

Kunes, Jiri ^{[1
]}

Pour, Milan ^{[1
]}

机构：

[1] Charles Univ Prague, Fac Pharm, Dept Inorgan & Organ Chem, Hradec Kralove 50005, Czech Republic

[2] Charles Univ Prague, Fac Pharm, Dept Analyt Chem, Hradec Kralove 50005, Czech Republic

[3] Univ Pardubice, Fac Chem Technol, Dept Gen & Inorgan Chem, Pardubice 53210, Czech Republic

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 03期

关键词：

OXIDATIVE ADDITION; ARYL TOSYLATES; PALLADIUM; NANOPARTICLES; COMPLEXES; CATALYSTS; CARBON; ALLYLATION; MECHANISMS; ANALOGS;

D O I：

10.1021/ol5035113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Migita-Stille coupling of (Z)-beta-iodoacrylates with (E)-a-stannyl allylic alcohols to furnish 5-alkylidene-4-substituted-5,6-dihydro-2H-pyran-2-ones is efficiently catalyzed by 2% Pd black in DMF, while Pd(PPh3)(4) is inactive. Heterogeneous Pd released in solution is most likely responsible for the catalysis. The reaction is applicable to other substrates, without having to resort to ligands, additives, and/or solid support for Pd. The resulting pyranones can be rearranged to fully functionalized pyranones in another single step.

引用

页码：520 / 523

页数：4

共 30 条

[1] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2 [J].