Synthesis of Highly Functionalized Biaryls by Condensation of 2-Fluoro-1,3-bis(silyloxy) 1,3-Dienes with 3-Cyanochromones and Subsequent Domino "Retro-Michael/Aldol/Fragmentation"

被引：15

作者：

Ibad, Muhammad Farooq ^{[1
]}

Abid, Obaid-ur-Rahman ^{[1
]}

Adeel, Muhammad ^{[1
,2
]}

Nawaz, Muhammad ^{[1
]}

Wolf, Verena ^{[1
]}

Villinger, Alexander ^{[1
]}

Langer, Peter ^{[1
,3
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Gomal Univ, Dept Chem, Dera Ismail Khan, Kpk, Pakistan

[3] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 23期

关键词：

1,3-BIS-SILYL ENOL ETHERS; ELECTROPHILIC FLUORINATION; METAL-FREE; CHEMISTRY;

D O I：

10.1021/jo1018443

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)-chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.

引用

页码：8315 / 8318

页数：4