Synthesis of 3-selanylbenzo[b]furans promoted by SelectFluor®

被引：25

作者：

Diem Ferreira Xavier, Mauricio Carpe ^{[1
]}

Andia Sandagorda, Eduardo Martarelo ^{[1
]}

Santos Neto, Jose Sebastiso ^{[3
]}

Schumacher, Ricardo Frederico ^{[1
,2
]}

Silva, Marcio Santos ^{[1
]}

机构：

[1] Univ Fed Pelotas UFPel, CCQFA, Lab Sintese Organ Limpa LASOL, Capao Do Leao, RS, Brazil

[2] Univ Fed Santa Maria, Dept Quim, Santa Maria, RS, Brazil

[3] Univ Fed Santa Catarina, Dept Quim, Florianopolis, SC, Brazil

来源：

RSC ADVANCES | 2020年 / 10卷 / 24期

关键词：

ELECTROPHILIC CYCLIZATION; CATALYST-FREE; IN-VITRO; FLUORINATION; MILD; ALCOHOLS; ALKYNES; CHEMISTRY; ANILINE; DESIGN;

D O I：

10.1039/d0ra01907k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and practical protocol for the synthesis of 3-selanyl-benzo[b]furans mediated by the SelectFluor (R) reagent was developed. This novel methodology provided a greener alternative to generate 3-substituted-benzo[b]furans via a metal-free procedure under mild conditions. The intramolecular cyclization reaction was carried out employing an electrophilic selenium species generated in situ through the reaction between SelectFluor (R) and organic diselenides. The formation of this electrophilic selenium species (RSe-F) was confirmed by heteronuclear NMR spectroscopy, and its reactivity was explored.

引用

页码：13975 / 13983

页数：9

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