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J Org Chem. 2013 Nov 15;78(22):11513-24. doi: 10.1021/jo402089r. Epub 2013 Nov 7.

An active, general, and long-lived palladium catalyst for cross-couplings of deactivated (hetero)aryl chlorides and bromides with arylboronic acids.

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1
Department of Chemistry and Chemical Engineering, Niigata University , 8050, 2-Nocho, Ikarashi, Nishi-ku, Niigata 950-2181, Japan.

Abstract

An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp(3))-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.

PMID:
24161157
DOI:
10.1021/jo402089r
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