Iron-catalyzed stereoselective haloamidation of amide-tethered alkynes

In this work, by using N -methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed formal cis -haloamidation of alkyne is reported. Without assistance of additives, the reaction worked well in the presence of 50 mol% FeCl 3 or FeBr 3 , leading to a series of chloro/bromo-containing...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-04, Vol.57 (35), p.4259-4262
Main Authors: Liu, Jin-Biao, Ren, Miaofeng, Lai, Xiaojing, Qiu, Guanyinsheng
Format: Article
Language:English
Subjects:
Additives
Alkynes
Crystallography
Ferric chloride
Iron
Stereoselectivity
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Summary:In this work, by using N -methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed formal cis -haloamidation of alkyne is reported. Without assistance of additives, the reaction worked well in the presence of 50 mol% FeCl 3 or FeBr 3 , leading to a series of chloro/bromo-containing isoindolin-5-ones with high efficiency and wide reaction scope. In the reaction, the iron-facilitated haloamidation proceeds through a halo anion-participating concerted [3+2] cyclization to release the final products. The key intermediate ferric acyl nitrene A is generated in situ from a formal removal of MeOH. In this work, by using N -methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed acyl nitrene/alkyne metalation-based chloramidation is reported for the synthesis of isoindol-5-ones.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc00870f