Porous Organic Polymer as a Heterogeneous Ligand for Highly Regio- and Stereoselective Nickel-Catalyzed Hydrosilylation of Alkyne

Zhou, Yun‐Bing; Liu, Zhikai; Fan, Xin-Yang; Li, Ren‐Hao; Zhang, Guoliang; Chen, Li; Pan, Ying‐Ming; Tang, Hai‐Tao; Zeng, Jia-Hao; Zhan, Zhuang‐Ping

doi:10.1021/acs.orglett.8b03064

Cited by 42 publications

(22 citation statements)

References 66 publications

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“…Hydrosilylation of phenylacetylene with PhSiH 3 catalyzed by complexes 2 – 4 has been also investigated. It was found that complexes 2 – 3 at room temperature performed low activity: 7 % conversion was reached in 48 h (Entries 13–14) [32c,i] . Compound 4 turned out to be inactive in this transformation.…”

Section: Resultsmentioning

confidence: 98%

Coordination Features of the 1,3,5‐Triazapentadienyl Ligand in Alkyl Complexes of Rare‐Earth Metals

et al. 2021

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The reactions of 1,3,5-triazapentadiene 2,6-iPr 2 C 6 H 3 NC(Ph) NC(Ph)NHC 6 H 3 iPr 2 -2,6 (1) with Ln(CH 2 SiMe 3 ) 3 (THF) 2 (Ln=Y, Lu) in hexane afford bis(alkyl) complexes [2,6-iPr 2 C 6 H 3 NC(Ph)NC(Ph) NC 6 H 3 iPr 2 -2,6]Ln(CH 2 SiMe 3 ) 2 (THF) (Ln=Y (2), Lu (3)) in 58 (2) and 62 (3) % yields. The X-ray diffraction study revealed that in 3 the triazapentadienyl ligand coordinates with the Lu 3 + ion in "amidinate" fashion resulting in the formation of a fourmembered metallocycle. In contrast, the reaction of 1 with the scandium analogue Sc(CH 2 SiMe 3 ) 3 (THF) 2 in toluene proceeds with the cleavage of CÀ N bond of 1,3,5-triazapentadiene and leads to the formation of a dinuclear monoalkyl complex [{μ 2 -2,6-iPr 2 C 6 H 3 NC(Ph)N}Sc(CH 2 SiMe 3 )(THF)] 2 (4) in 43 % yield. Complex 4 features k 2 -N,N-coordination of the residual dianionic {μ 2 -2,6-iPr 2 C 6 H 3 NC(Ph)N} 2À ligand μ-bridging two Sc 3 + centers. Alkyl complexes 2-4 were evaluated as pre-catalysts for isoprene polymerization and hydrosilylation of unsaturated substrates with PhSiH 3 .

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Section: Resultsmentioning

confidence: 98%

Coordination Features of the 1,3,5‐Triazapentadienyl Ligand in Alkyl Complexes of Rare‐Earth Metals

et al. 2021

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“…[98] Furthermore,isolated Ni centers stabilized by heterogeneous ligands have been applied for hydrosilylation reactions very recently.I nt his latter case, ap orous organic polymer containing Xantphos (POP-Xantphos) moieties was used to stabilize the isolated nickel centers.T he prepared Ni-POP-Xantphos catalyst demonstrated high regio-and stereoselectivity in the hydrosilylation of alkynes.T he obtained selectivity was considered to be controlled by the microporous structure of POP-Xantphos. [99] Figure 4. Characterization of the Pt-ISA/NG catalyst:a)T ypical transmission electron microscopy( TEM) image.…”

Section: Other Precious Metal Catalystsmentioning

confidence: 99%

Recent Advances in Catalytic Hydrosilylations: Developments beyond Traditional Platinum Catalysts

et al. 2020

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“…The prepared Ni‐POP‐Xantphos catalyst demonstrated high regio‐ and stereoselectivity in the hydrosilylation of alkynes. The obtained selectivity was considered to be controlled by the microporous structure of POP‐Xantphos [99] …”

Section: Recyclable Heterogeneous Catalystsmentioning

confidence: 99%

“…[98] Furthermore,isolated Ni centers stabilized by heterogeneous ligands have been applied for hydrosilylation reactions very recently.I nt his latter case, ap orous organic polymer containing Xantphos (POP-Xantphos) moieties was used to stabilize the isolated nickel centers.T he prepared Ni-POP-Xantphos catalyst demonstrated high regio-and stereoselectivity in the hydrosilylation of alkynes.T he obtained selectivity was considered to be controlled by the microporous structure of POP-Xantphos. [99] [93] Copyright2 018, American Chemical Society. Scheme 28.…”

Section: Nickel-based Heterogeneous Catalystsmentioning

confidence: 99%

Recent Advances in Catalytic Hydrosilylations: Developments beyond Traditional Platinum Catalysts

et al. 2020

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Hydrosilylation reactions, which allow the addition of Si−H to C=C/C≡C bonds, are typically catalyzed by homogeneous noble metal catalysts (Pt, Rh, Ir, and Ru). Although excellent activity and selectivity can be obtained, the price, purification, and metal residues of these precious catalysts are problems in the silicone industry. Thus, a strong interest in more sustainable catalysts and for more economic processes exists. In this respect, recently disclosed hydrosilylations using catalysts based on earth‐abundant transition metals, for example, Fe, Co, Ni, and Mn, and heterogeneous catalysts (supported nanoparticles and single‐atom sites) are noteworthy. This minireview describes the recent advances in this field.

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Porous Organic Polymer as a Heterogeneous Ligand for Highly Regio- and Stereoselective Nickel-Catalyzed Hydrosilylation of Alkyne

Cited by 42 publications

References 66 publications

Coordination Features of the 1,3,5‐Triazapentadienyl Ligand in Alkyl Complexes of Rare‐Earth Metals

Coordination Features of the 1,3,5‐Triazapentadienyl Ligand in Alkyl Complexes of Rare‐Earth Metals

Recent Advances in Catalytic Hydrosilylations: Developments beyond Traditional Platinum Catalysts

Recent Advances in Catalytic Hydrosilylations: Developments beyond Traditional Platinum Catalysts

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