Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides

Anne Eeg Jensen; Paul Knochel

doi:10.1021/jo0105787

Nickel-catalyzed cross-coupling between functionalized primary or secondary alkylzinc halides and primary alkyl halides

J Org Chem. 2002 Jan 11;67(1):79-85. doi: 10.1021/jo0105787.

Authors

Anne Eeg Jensen¹, Paul Knochel

Affiliation

¹ Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 Munich, Germany.

PMID: 11777442
DOI: 10.1021/jo0105787

Abstract

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.