1. Annulative π-Extension (APEX) of Heteroarenes with Dibenzosiloles and Dibenzogermoles by Palladium/o-Chloranil Catalysis
- Author
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Kyohei Ozaki, Wataru Matsuoka, Hideto Ito, and Kenichiro Itami
- Subjects
O-chloranil ,010405 organic chemistry ,Organic Chemistry ,Cationic polymerization ,Benzothiophene ,chemistry.chemical_element ,Germanium ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Biochemistry ,Cycloaddition ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,chemistry ,Polymer chemistry ,Physical and Theoretical Chemistry ,Benzofuran ,Palladium - Abstract
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.
- Published
- 2017
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