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Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs

By Fabrice Chemla, Florian Dulong, Franck Ferreira and Alejandro P&#233


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 &#946;-(propargyloxy)enoates having pendant iodo- and bromoalkynes, is disclosed. Formation of the carbenoid intermediate is fully stereoselective at &#8722;30 &#176;C and arises from a formal <i>anti</i>-selective carbozincation reaction. Upon warming, the zinc carbenoid is stereochemically labile and isomerizes to its more stable form

Topics: carbenoids, carbometallation, carbozincation, radicals, tandem reaction, Organic chemistry, QD241-441, Chemistry, QD1-999, Science, Q, DOAJ:Organic Chemistry, DOAJ:Chemistry
Publisher: Beilstein-Institut
Year: 2013
DOI identifier: 10.3762/bjoc.9.28
OAI identifier: oai:doaj.org/article:0443e74070b64ea1bc0ae5c6dc71abe0
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