Annulative π-Extension (APEX) of Heteroarenes with Dibenzosiloles and Dibenzogermoles by Palladium/o-Chloranil Catalysis,Organic Letters

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Annulative π-Extension (APEX) of Heteroarenes with Dibenzosiloles and Dibenzogermoles by Palladium/o-Chloranil Catalysis
Organic Letters ( IF 4.9 ) Pub Date : 2017-03-30 00:00:00 , DOI: 10.1021/acs.orglett.7b00684
Kyohei Ozaki ₁ , Wataru Matsuoka ₁ , Hideto Ito ₁ , Kenichiro Itami _{1,

2,

3}

Affiliation

Annulative π-extension (APEX) reactions of heteroarenes are described herein. A catalytic system comprising a cationic palladium species and o-chloranil using dimethyldibenzosiloles as π-extending agents enabled the extension of the π-system of benzo[b]thiophenes. π-Extended dibenzofurans and carbazoles could also be obtained from benzofuran and N-tosylindole, respectively, with dimethyldibenzogermole as a germanium-based π-extending agent. Mechanistic investigations indicated two possible reaction pathways involving carbopalladation-based double C–H arylation of benzothiophene or formal cycloaddition/oxidation cascades.

中文翻译：

钯/邻氯苯腈催化杂芳烃与二苯并甲硅烷基和二苯并germol的环形π扩展（APEX）

本文描述了杂芳烃的环状π-延伸（APEX）反应。使用二甲基二苯并甲硅烷作为π扩展剂的包含阳离子钯物种和邻氯甲腈的催化体系使苯并[ b ]噻吩的π系统得以扩展。π-扩展的二苯并呋喃和咔唑也可以分别从二甲基呋喃和锗的π-扩展剂分别从苯并呋喃和N-甲苯磺酰基吲哚得到。机理研究表明，两种可能的反应途径涉及基于碳链的苯并噻吩的双CH芳基化反应或正式的环加成/氧化级联反应。

更新日期：2017-03-30

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