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  • Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal.

Rhodium-catalyzed direct annulation of aldehydes with alkynes leading to indenones: proceeding through in situ directing group formation and removal.

Organic letters (2013-09-10)
Shuyou Chen, Jintao Yu, Yan Jiang, Fan Chen, Jiang Cheng
RESUMEN

The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.

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Sigma-Aldrich
Benzaldehyde, purified by redistillation, ≥99.5%
Sigma-Aldrich
Benzaldehyde, ReagentPlus®, ≥99%
Sigma-Aldrich
Benzaldehyde, ≥98%, FG, FCC
Sigma-Aldrich
Rhodium, powder, 99.95% trace metals basis
Sigma-Aldrich
Benzaldehyde, natural, FCC, FG
Supelco
Benzaldehyde, Pharmaceutical Secondary Standard; Certified Reference Material
Benzaldehyde, European Pharmacopoeia (EP) Reference Standard