Nickel-Catalyzed Cross-Coupling between Functionalized Primary or Secondary Alkylzinc Halides and Primary Alkyl Halides

Autor:	Paul Knochel, Anne Eeg Jensen
Rok vydání:	2001
Předmět:	chemistry.chemical_classification Primary (chemistry) Nitrile Bicyclic molecule Organic Chemistry Alkylation law.invention chemistry.chemical_compound chemistry law Amide Polymer chemistry Organic chemistry Chemoselectivity Walden inversion Alkyl
Zdroj:	The Journal of Organic Chemistry. 67:79-85
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo0105787
Popis:	In the presence of Bu(4)NI (3 equiv) and 4-fluorostyrene (20 mol %), unreactive primary and secondary alkylzinc iodides undergo nickel-catalyzed cross-couplings with various primary alkyl iodides or bromides. More reactive secondary dialkylzincs and the mixed zinc organometallics RZnTMSM undergo the cross-coupling reaction in the absence of Bu(4)NI. The bicyclic secondary diorganozinc 6 prepared via boron-zinc exchange reacts with high retention of configuration. Free NH-groups are tolerated in the cross-coupling allowing the synthesis of aminated products.
Databáze:	OpenAIRE
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