Direct Synthesis of Benzoselenophene and Benzothiophene Derivatives from 1,1-Diarylethenes and Biaryls by Chalcogen Cation-Mediated Successive Bond Formation

被引：2

作者：

Iwamoto, Hiroki ^{[1
]}

Kojima, Yuki ^{[1
]}

Nishimura, Kazutoshi ^{[1
]}

Yasui, Kosuke ^{[1
]}

Hirano, Koji ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTRI, Innovat Catalysis Sci Div, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 05期

基金：

日本学术振兴会;

关键词：

SOLAR-CELLS; CONJUGATED POLYMERS; SELENOPHENE; SEMICONDUCTORS;

D O I：

10.1021/acs.orglett.3c04033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Tf2O-mediated sequential C-Se bond-forming reaction of 1,1-diarylethenes and biaryls with methaneselenic acid has been developed. Upon demethylation workup with ethanolamine, the corresponding benzoselenophene derivatives are obtained directly. The related synthesis of benzothiophene derivatives with sodium methanesulfinate is also possible with the unique assistance of the ball milling technique. The active species is considered to be a highly electrophilic chalcogen cation, which enables successive bond formation even at room temperature.

引用

页码：1006 / 1010

页数：5