New trans-chelating ligands and their complexes and catalytic properties in the Mizoroki - Heck arylation of cyclohexene

Luba Kaganovsky; Kyung Bin Cho; Dmitri Gelman

doi:10.1021/om800448b

New trans-chelating ligands and their complexes and catalytic properties in the Mizoroki - Heck arylation of cyclohexene

Luba Kaganovsky, Kyung Bin Cho, Dmitri Gelman^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

Abstract

New air-stable chelating diphosphine ligands, 1,8-bis(4-(diphenylphosphino) phenyl)anthracene (2) and 1,8-bis(4-(diphenylphosphino)-3,5-dimethylphenyl) anthracene (3), were synthesized from readily available starting materials. The examination of their coordination modes in Pd(II) and Rh(I) complexes by means of ¹H, ¹³C, and ³¹P NMR spectroscopy and X-ray analysis revealed that 2 is mainly a trans-coordinating ligand but can also adapt smaller coordination angles, while 3 is "purely" trans-spanning and no formation of identifiable cis-chelated complexes was detected. The catalytic activity of the new compounds was tested in palladium-catalyzed Mizoroki-Heck reactions of aryl bromides with cyclohexene.

Original language	English
Pages (from-to)	5139-5145
Number of pages	7
Journal	Organometallics
Volume	27
Issue number	19
DOIs	https://doi.org/10.1021/om800448b
State	Published - 13 Oct 2008

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abstract = "New air-stable chelating diphosphine ligands, 1,8-bis(4-(diphenylphosphino) phenyl)anthracene (2) and 1,8-bis(4-(diphenylphosphino)-3,5-dimethylphenyl) anthracene (3), were synthesized from readily available starting materials. The examination of their coordination modes in Pd(II) and Rh(I) complexes by means of 1H, 13C, and 31P NMR spectroscopy and X-ray analysis revealed that 2 is mainly a trans-coordinating ligand but can also adapt smaller coordination angles, while 3 is {"}purely{"} trans-spanning and no formation of identifiable cis-chelated complexes was detected. The catalytic activity of the new compounds was tested in palladium-catalyzed Mizoroki-Heck reactions of aryl bromides with cyclohexene.",

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T1 - New trans-chelating ligands and their complexes and catalytic properties in the Mizoroki - Heck arylation of cyclohexene

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AU - Cho, Kyung Bin

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N2 - New air-stable chelating diphosphine ligands, 1,8-bis(4-(diphenylphosphino) phenyl)anthracene (2) and 1,8-bis(4-(diphenylphosphino)-3,5-dimethylphenyl) anthracene (3), were synthesized from readily available starting materials. The examination of their coordination modes in Pd(II) and Rh(I) complexes by means of 1H, 13C, and 31P NMR spectroscopy and X-ray analysis revealed that 2 is mainly a trans-coordinating ligand but can also adapt smaller coordination angles, while 3 is "purely" trans-spanning and no formation of identifiable cis-chelated complexes was detected. The catalytic activity of the new compounds was tested in palladium-catalyzed Mizoroki-Heck reactions of aryl bromides with cyclohexene.

AB - New air-stable chelating diphosphine ligands, 1,8-bis(4-(diphenylphosphino) phenyl)anthracene (2) and 1,8-bis(4-(diphenylphosphino)-3,5-dimethylphenyl) anthracene (3), were synthesized from readily available starting materials. The examination of their coordination modes in Pd(II) and Rh(I) complexes by means of 1H, 13C, and 31P NMR spectroscopy and X-ray analysis revealed that 2 is mainly a trans-coordinating ligand but can also adapt smaller coordination angles, while 3 is "purely" trans-spanning and no formation of identifiable cis-chelated complexes was detected. The catalytic activity of the new compounds was tested in palladium-catalyzed Mizoroki-Heck reactions of aryl bromides with cyclohexene.

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New trans-chelating ligands and their complexes and catalytic properties in the Mizoroki - Heck arylation of cyclohexene

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