Transition-Metal-Catalyzed Additions of Silicon−Silicon and Silicon−Heteroatom Bonds to Unsaturated Organic Molecules

Suginome, Michinori; Ito, Yoshihiko

doi:10.1021/cr9902805

Cited by 408 publications

(154 citation statements)

References 148 publications

(293 reference statements)

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“…183 The resulting silylstannanes can be added across unsaturated bonds via palladium catalyst to afford a bifunctional organic dianion equivalent containing both carbon-silicon and carbon-tin bonds (Scheme 42). [184][185][186][187][188] These products can be selectively destannylated or desilylated, or silyl, stannyl groups can be substituted or the stannyl groups can participate in the Stille couplings. As the addition of silylstannanes across unsaturated systems uses expensive palladium catalysts, immobilization of the palladium catalyst in ILs that allows recycling of the catalyst without loss of activity was seen as a potentially useful application of the ILs in the organic synthesis.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Ionic liquids: a versatile medium for palladium-catalyzed reactions

Singh¹,

Sharma²,

Mamgain³

et al. 2008

J. Braz. Chem. Soc.

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Um grande número de reações de formação de ligações carbono-carbono (tais como: acoplamentos de Heck, Suzuki, Stille, Negishi e Sonogashira, entre outros) é facilitado pela catálise com compostos de paládio. Neste artigo de revisão, apresentamos uma visão detalhada e compreensiva da literatura sobre a versatilidade do uso de líquidos iônicos em conjunto com paládio em vários tipos de reações.A number of carbon-carbon bond forming reactions in organic chemistry (such as the Heck, Suzuki, Stille, Negishi, Sonogashira coupling etc) are facilitated by catalysis with palladium compounds. An attempt has been made to present a detailed and comprehensive literature collection about the versatility of ionic liquid in conjunction with palladium for various types of reactions.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Ionic liquids: a versatile medium for palladium-catalyzed reactions

Singh¹,

Sharma²,

Mamgain³

et al. 2008

J. Braz. Chem. Soc.

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“…No diastereomeric products were observed in any reaction. No product was observed when Pt(acac) 2 was replaced by Ni(acac) 2 .…”

Section: Communications Martin Gerdin Christina Moberg Was Observed mentioning

confidence: 99%

“…Changing the Ni source to Ni(COD) 2 resulted in an inferior catalyst, affording only low conversion to product. We were not able to find any useful catalyst based on palladium; a number of palladium complexes prepared from Pd 2 (dba) 3 , Pd(acac) 2 , Pd(OAc) 2 , bis[(h 3 -allyl)palladium chloride], with or without DI-BALH, and cyclohexyldiphenylphosphine or triphenylphosphine were tested at 80 8C and 110 8C, but no product was observed. In contrast, platinum complexes with a wider range of ligand structures turned out to serve as catalysts.…”

mentioning

confidence: 98%

Enantioselective Platinum‐Catalyzed Silicon‐Boron Addition to 1,3‐Cyclohexadiene

Gerdin

Moberg

2005

Adv Synth Catal

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“…Among these catalytic conversions, the oxidative addition of hydrosilanes with platinum(0) complexes is an efficient method for the generation of the platinum(II) hydride species, which has been proposed as a key intermediate in platinum-catalyzed hydrosilylations [2][3][4][5][6] and bis-silylations [7,8], as well as the dehydrogenative couplings of hydrosilanes [9][10][11][12][13]. While a number of reactions of hydrosilanes with platinum(0) complexes affording mononuclear bis(silyl) [14][15][16][17][18] and silyl-bridged multinuclear complexes [19][20][21][22][23][24][25][26][27][28][29] have been described so far, the isolation of mononuclear hydrido(silyl) complexes has been less well studied due to the high reactivity of a Pt-H bond [30][31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Si–H Bond Activation of a Primary Silane with a Pt(0) Complex: Synthesis and Structures of Mononuclear (Hydrido)(dihydrosilyl) Platinum(II) Complexes

et al. 2017

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Abstract:A hydrido platinum(II) complex with a dihydrosilyl ligand, [cis-PtH(SiH 2 Trip)(PPh 3 ) 2 ] (2) was prepared by oxidative addition of an overcrowded primary silane, TripSiH 3 (1, Trip = 9-triptycyl) with [Pt(η 2 -C 2 H 4 )(PPh 3 ) 2 ] in toluene. The ligand-exchange reactions of complex 2 with free phosphine ligands resulted in the formation of a series of (hydrido)(dihydrosilyl) complexes (3-5). Thus, the replacement of two PPh 3 ligands in 2 with a bidentate bis(phosphine) ligand such asIn contrast, the ligand-exchange reaction of 2 with an excess amount of PMe 3 in toluene quantitatively produced [PtH(SiH 2 Trip)(PMe 3 )(PPh 3 )] (5), where the PMe 3 ligand is adopting trans to the hydrido ligand. The structures of complexes 2-5 were fully determined on the basis of their NMR and IR spectra, and elemental analyses. Moreover, the low-temperature X-ray crystallography of 2, 3, and 5 revealed that the platinum center has a distorted square planar environment, which is probably due to the steric requirement of the cis-coordinated phosphine ligands and the bulky 9-triptycyl group on the silicon atom.

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Transition-Metal-Catalyzed Additions of Silicon−Silicon and Silicon−Heteroatom Bonds to Unsaturated Organic Molecules

Cited by 408 publications

References 148 publications

Ionic liquids: a versatile medium for palladium-catalyzed reactions

Ionic liquids: a versatile medium for palladium-catalyzed reactions

Enantioselective Platinum‐Catalyzed Silicon‐Boron Addition to 1,3‐Cyclohexadiene

Si–H Bond Activation of a Primary Silane with a Pt(0) Complex: Synthesis and Structures of Mononuclear (Hydrido)(dihydrosilyl) Platinum(II) Complexes

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