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

In the presence of Bu4NI (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 c...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-01, Vol.67 (1), p.79-85
Main Authors: Jensen, Anne Eeg, Knochel, Paul
Format: Article
Language:English
Subjects:
Al, ga, in, tl, zn, cd, hg derivatives
Chemistry
Exact sciences and technology
Organic chemistry
Organometalloidal and organometallic compounds
Preparations and properties
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Summary:In the presence of Bu4NI (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 Bu4NI. 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0105787