Friedel-Crafts-Type Reactions with Electrochemically Generated Electrophiles from Donor-Acceptor Cyclopropanes and -Butanes

被引：41

作者：

Kolb, Simon ^{[1
]}

Ahlburg, Nils L. ^{[1
]}

Werz, Daniel B. ^{[1
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 14期

关键词：

BRONSTED ACID; CYCLOBUTANES; CYCLOADDITION; ANNULATION; STRAIN; CONSTRUCTION; ALKYLATION; ION;

D O I：

10.1021/acs.orglett.1c01890

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a general electrochemical method to functionalize donor-acceptor (D-A) cyclopropanes and -butanes with arenes utilizing Friedel-Crafts-type reactivity. The catalyst-free strategy relies on the direct anodic oxidation of the strained carbocycles, which leads after C(sp(3))-C(sp(3)) cleavage to radical cations that act as electrophiles for the arylation reaction. Broad reaction scopes in regard to cyclopropanes, cyclobutanes, and aromatic reaction partners are presented. Additionally, a plausible electrolysis mechanism is proposed.

引用

页码：5549 / 5553

页数：5

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