Palladium complexes bearing novel strongly bent trans-spanning diphosphine ligands: Synthesis, characterization, and catalytic activity

Olga Grossman, Clarit Azerraf, Dmitri Gelman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

The new air-stable chelating diphosphine ligands 1,8- bis(diisopropylphosphino)triptycene (2) and 1-(diisopropylphosphino)-8- (diphenylphosphino)triptycene (3) were synthesized in 51-73% yield from readily available starting materials. The examination of their coordination modes in the palladium(II) complexes [PdCl2(2)] (4) and [PdCl2(3)] (5) by means of 1H, 13C, and 31P NMR is consistent with the formation of trans-spanned complexes. X-ray analysis of 4 and 5 confirmed the structure but disclosed a strong distortion of the palladium centers from the expected square-planar geometry toward a butterfly-like environment. Further investigation revealed that 2 can also behave as a binucleating ligand, forming the quasi-closed halogen-bridged dipalladium complex 6, featuring an unusual nonplanar Pd2(μ-Cl) 2Cl2 core. The catalytic activity of the new ligands and complexes was tested in palladium-catalyzed cross-coupling reactions of aryl chlorides with phenylboronic acid.

Original languageAmerican English
Pages (from-to)375-381
Number of pages7
JournalOrganometallics
Volume25
Issue number2
DOIs
StatePublished - 16 Jan 2006

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