Graphene Oxide Promotes Site-Selective Allylic Alkylation of Thiophenes with Alcohols

被引：26

作者：

Favaretto, Laura ^{[2
]}

An, Juzeng ^{[1
]}

Sambo, Marco ^{[1
]}

De Nisi, Assunta ^{[1
]}

Bettini, Cristian ^{[2
]}

Melucci, Manuela ^{[2
]}

Kovtun, Alessandro ^{[2
]}

Liscio, Andrea ^{[2
,3
]}

Palermo, Vincenzo ^{[2
]}

Bottoni, Andrea ^{[1
]}

Zerbetto, Francesco ^{[1
]}

Calvaresi, Matteo ^{[1
]}

Bandini, Marco ^{[1
]}

机构：

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

[2] CNR, ISOF, Via Gobetti 101, I-40129 Bologna, Italy

[3] CNR, IMM, Via Fosso del Cavaliere 100, I-00133 Rome, Italy

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 12期

关键词：

FRIEDEL-CRAFTS ALKYLATION; GOLD-CATALYZED SYNTHESIS; SOLVENT-FREE CONDITIONS; GRAPHITE OXIDE; CARBON NANOTUBES; CASCADE REACTION; S(N)2 REACTION; INDOLES; CARBOCATALYSIS; OXIDATION;

D O I：

10.1021/acs.orglett.8b01531

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The graphene oxide (GO) assisted allylic alkylation of thiophenes with alcohols is presented. Mild reaction conditions and a low GO loading enabled the isolation of a range of densely functionalized thienyl and bithienyl compounds in moderate to high yields (up to 90%). The cooperative action of the Bronsted acidity, epoxide moieties, and pi-surface of the 2D-promoter is highlighted as crucial in the reaction course of the present Friedel-Crafts-type protocol.

引用

页码：3705 / 3709

页数：5

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