Gold-Catalyzed Dearomatization of 2-Naphthols with Alkynes

被引：35

作者：

An, Juzeng ^{[1
]}

Parodi, Adriano ^{[1
]}

Monari, Magda ^{[1
]}

Castineira Reis, Marta ^{[2
]}

Silva Lopez, Carlos ^{[2
]}

Bandini, Marco ^{[1
]}

机构：

[1] Univ Bologna, Alma Mater Studiorum, Dipartimento Chim G Ciamician, Via Selmi 2, I-40126 Bologna, Italy

[2] Univ Vigo, Dept Quim Organ, Vigo 36310, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 69期

关键词：

catalysis; dearomatization; gold; mechanism; naphthol; INTERMOLECULAR ARYLATIVE DEAROMATIZATION; ASYMMETRIC DEAROMATIZATION; BETA-NAPHTHOLS; INTRAMOLECULAR DEAROMATIZATION; OXIDATIVE DEAROMATIZATION; NONCOVALENT INTERACTIONS; INDOLES; ALCOHOLS; CONSTRUCTION; IRIDIUM;

D O I：

10.1002/chem.201704942

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The site-selective dearomatization of naphthols is realized in a straightforward manner through a gold(I)-catalyzed [3,3]-sigmatropic rearrangement/allene functionalization cascade sequence. The method employs readily available naphthylpropargyl ethers as starting materials. A range of densely functionalized dihydrofurylnaphthalen-2(1H)-ones are obtained in high yields (up to 98%) and extremely mild reaction conditions (reagent grade solvent, air, 10minute reaction time). A complete theoretical elucidation of the reaction machinery is also proposed, providing a rationale for important issues such as regio- and chemoselectivity.

引用

页码：17473 / 17477

页数：5

共 87 条

[1] Gold-Catalyzed Cyclization Reactions of Allenol and Alkynol Derivatives [J].