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Intramolecular Arene C-H to C-P Functionalization Mediated by Ni(II) and Pd(II).

ABSTRACT: A trisphosphine ligand with a triarylbenzene backbone was employed to support mono-nickel(II) and palladium(II) complexes. Two phosphine arms coordinated to the metal center, while the third phosphine was found to form a C-P bond with dearomatization of the central arene. Deprotonation effected the rearomatization of the central ring and metal reduction from M(II) to M(0). The overall conversion corresponds to a functionalization of an unactivated arene C-H bond to a C-P bond. This transformation represents a rare type of mechanism of C-H functionalization, facilitated by the interactions of the group 10 metal with the arene ?-system. This conversion is reminiscent of and expands the scope of recently reported intramolecular rearrangements of biaryl phosphine ligands common in group 10 catalysis.

SUBMITTER: Suseno S

PROVIDER: S-EPMC3811949 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Intramolecular Arene C-H to C-P Functionalization Mediated by Ni(II) and Pd(II).

Suseno Sandy S Agapie Theodor T

Organometallics 20130601 11

A trisphosphine ligand with a triarylbenzene backbone was employed to support mono-nickel(II) and palladium(II) complexes. Two phosphine arms coordinated to the metal center, while the third phosphine was found to form a C-P bond with dearomatization of the central arene. Deprotonation effected the rearomatization of the central ring and metal reduction from M(II) to M(0). The overall conversion corresponds to a functionalization of an unactivated arene C-H bond to a C-P bond. This transformatio ...[more]

PMID: 24187424

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