η<sup>3</sup>‐Vinylborane Complexes of Platinum and Nickel: Borataallyl‐ and Alkyl/Borataalkene‐Like Coordination Modes

Kolpin, Kristopher B.; Emslie, David J. H.

doi:10.1002/ange.200906931

Angewandte Chemie

2010

DOI: 10.1002/ange.200906931

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η³‐Vinylborane Complexes of Platinum and Nickel: Borataallyl‐ and Alkyl/Borataalkene‐Like Coordination Modes

Kristopher B. Kolpin

David J. H. Emslie

Abstract: Feiner Unterschied: Das Vinylboran PhHCCH‐B(C6F5)2 reagiert mit nullwertigen Übergangsmetallspezies der Gruppe 10 zu η3‐Vinylboran‐Komplexen. Der Platin‐PtBu3‐Komplex zeigt eine η3‐Borataallyl‐artige Koordination, während der Nickel‐(Ph3P)2‐Komplex eine Alkyl‐/Borataalken‐Koordination bevorzugt.

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Cited by 7 publications

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“…Alkenylboron compounds are widely used in organic synthesis, 8 photochemistry, 9 and coordination chemistry. 10 In particular, they are used as alkenyl reagents in coupling reactions for the preparation of substituted alkenes. 8a The products 2 all contain a reactive boryl substituent.…”

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Carbon−Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes

et al. 2010

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Carbon−Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes

et al. 2010

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ortho‐(Dimesitylboryl)phenylphosphines: Positive Boryl Effect in the Palladium‐Catalyzed Suzuki–Miyaura Coupling of 2‐Chloropyridines

Malacea¹,

Chahdoura²,

Devillard³

et al. 2013

Adv Synth Catal

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Catalytic systems combining ortho-(dimesitylboryl)phenylphosphines and palladium precursors have been evaluated in the Suzuki-Miyaura couplings of chloro-N-heterocycles, in particular 2-chloroA C H T U N G T R E N N U N G pyridines, with arylboronic acids. The Lewis basic character of the substrates does not interfere with the Lewis acidic site of the ligands, even for a substrate featuring free NH 2 groups. The influence of several reaction parameters has been studied and the ortho-dimesitylboryl moiety was actually found to substantially enhance the catalytic performance. The role of this group has been examined using preformed phosphine-borane/Pd complexes and the formation of an original phosphine/h 4 -boratabutadiene complex has been identified as a possible deactivation pathway. Regioselective coupling of 2,6-dichloro-3-nitropyridine with phosphine-borane/Pd catalysts has also been explored, and sequential double cross-couplings were found to give a direct and efficient access to unsymmetrical 2,6-diarylpyridines.

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Hypervalent Silicon Compounds by Coordination of Diphosphine–Silanes to Gold

Gualco

Mercy

Ladeira³

et al. 2010

Chemistry A European J

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Coordination of ambiphilic diphosphine-silane ligands [o-(iPr(2)P)C(6)H(4)](2)Si(R)F (R=F, Ph, Me) to AuCl affords pentacoordinate neutral silicon compounds in which the metal atom acts as a Lewis base. X-ray diffraction analyses, NMR spectroscopy, and DFT calculations substantiate the presence of Au→Si interactions in these complexes, which result in trigonal-bipyramidal geometries around silicon. The presence of a single electron-withdrawing fluorine atom is sufficient to observe coordination of the silane as a σ-acceptor ligand, provided it is positioned trans to gold. The nature of the second substituent at silicon (R=F, Ph, Me) has very little influence on the magnitude of the Au→Si interaction, in marked contrast to N→Si adducts. According to variable-temperature and 2D EXSY NMR experiments, the apical/equatorial positions around silicon exchange in the slow regime of the NMR timescale. The two forms, with the fluorine atom in trans or cis position to gold, were characterized spectroscopically and the activation barrier for their interconversion was estimated. The bonding and relative stability of the two isomeric structures were assessed by DFT calculations.

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η³‐Vinylborane Complexes of Platinum and Nickel: Borataallyl‐ and Alkyl/Borataalkene‐Like Coordination Modes

Cited by 7 publications

References 49 publications

Carbon−Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes

Carbon−Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes

ortho‐(Dimesitylboryl)phenylphosphines: Positive Boryl Effect in the Palladium‐Catalyzed Suzuki–Miyaura Coupling of 2‐Chloropyridines

Hypervalent Silicon Compounds by Coordination of Diphosphine–Silanes to Gold

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η3‐Vinylborane Complexes of Platinum and Nickel: Borataallyl‐ and Alkyl/Borataalkene‐Like Coordination Modes

Cited by 7 publications

References 49 publications

Carbon−Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes

Carbon−Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes

ortho‐(Dimesitylboryl)phenylphosphines: Positive Boryl Effect in the Palladium‐Catalyzed Suzuki–Miyaura Coupling of 2‐Chloropyridines

Hypervalent Silicon Compounds by Coordination of Diphosphine–Silanes to Gold

Contact Info

Product

Resources

About

η³‐Vinylborane Complexes of Platinum and Nickel: Borataallyl‐ and Alkyl/Borataalkene‐Like Coordination Modes