Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs
| Autor: | Florian Dulong, Alejandro Perez-Luna, Fabrice Chemla, Franck Ferreira |
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| Přispěvatelé: | Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
Radical
Dimethylzinc carbozincation chemistry.chemical_element Zinc 010402 general chemistry Zinc atom 01 natural sciences Full Research Paper lcsh:QD241-441 chemistry.chemical_compound Cascade reaction lcsh:Organic chemistry Polymer chemistry Organic chemistry tandem reaction lcsh:Science Carbenoid Alkyl chemistry.chemical_classification 010405 organic chemistry carbometallation [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry radicals 3. Good health 0104 chemical sciences Chemistry chemistry 13. Climate action Stereoselectivity lcsh:Q carbenoids |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Beilstein-Institut, 2013, 9, pp.236-245. ⟨10.3762/bjoc.9.28⟩ Beilstein Journal of Organic Chemistry, Vol 9, Iss 1, Pp 236-245 (2013) Beilstein Journal of Organic Chemistry, 2013, 9, pp.236-245. ⟨10.3762/bjoc.9.28⟩ |
| ISSN: | 1860-5397 |
| Popis: | 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-(propargyloxy)enoates 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 carbozincation reaction. Upon warming, the zinc carbenoid is stereochemically labile and isomerizes to its more stable form. |
| Databáze: | OpenAIRE |
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