Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincsReport as inadecuate




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1 IPCM - Institut Parisien de Chimie Moléculaire

Abstract : The formation of alkylidenezinc carbenoids by 1,4-addition-carbozincation of dialkylzincs or alkyl iodides based on zinc atom radical transfer, in the presence of dimethylzinc with β-propargyloxyenoates having pendant iodo-and bromoalkynes, is disclosed. Formation of the carbenoid intermediate is fully stereoselective at −30 °C and arises from a formal anti-selective carbo-zincation reaction. Upon warming, the zinc carbenoid is stereochemically labile and isomerizes to its more stable form.

Keywords : tandem reaction radicals carbometallation carbozincation carbenoids





Author: Fabrice Chemla - Florian Dulong - Franck Ferreira - Alejandro Pérez-Luna -

Source: https://hal.archives-ouvertes.fr/



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