Photocatalytic C–X borylation of aryl halides by hierarchical SiC nanowire-supported Pd nanoparticles

Jiao, Zhifeng; Zhao, Ji-Xiao; Guo, Xiaoning; Guo, Xiang‐Yun

doi:10.1016/s1872-2067(19)63449-2

Cited by 16 publications

(5 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Guo et al developed a heterogeneous borylation protocol that employs hierarchical silicon carbide (SiC) nanowire-supported Pd nanoparticles as a photocatalyst to convert aryl bromides and iodides to the corresponding borylated products in excellent yields under visible-light irradiation (400−800 nm) at 30 °C. 97 Besides transition metal photocatalysis, organic photoredox catalysis can also afford high reactivity, allowing access to selective transformations of a large variety of substrates that have low activity in most traditional synthetic strategies. 63 Most photoinduced organocatalysis involve a radical pathway.…”

Section: Photoinduced C−x Borylationmentioning

confidence: 99%

See 1 more Smart Citation

Photoinduced Borylation for the Synthesis of Organoboron Compounds

et al. 2021

Self Cite

View full text Add to dashboard Cite

Organoboron compounds have important synthetic value and can be applied in numerous transformations. The development of practical and convenient ways to synthesize boronate esters has thus attracted significant interest. Photoinduced borylations originated from stoichiometric reactions of alkanes and arenes with well-defined metal–boryl complexes. Now, photoredox-initiated borylations, catalyzed by either transition metal or organic photocatalysts, and photochemical borylations with high efficiency have become a burgeoning area of research. In this Focus Review, we summarize research on photoinduced borylations, especially emphasizing recent developments and trends. This includes the photoinduced borylation of arenes, alkanes, aryl/alkyl halides, activated carboxylic acids, amines, alcohols, and so on based on transition metal catalysis, metal-free organocatalysis, and direct photochemical activation. We focus on reaction mechanisms involving single-electron transfer, triplet-energy transfer, and other radical processes.

show abstract

Section: Photoinduced C−x Borylationmentioning

confidence: 99%

“…Guo et al. developed a heterogeneous borylation protocol that employs hierarchical silicon carbide (SiC) nanowire-supported Pd nanoparticles as a photocatalyst to convert aryl bromides and iodides to the corresponding borylated products in excellent yields under visible-light irradiation (400–800 nm) at 30 °C …”

Section: Photoinduced C–x Borylationmentioning

confidence: 99%

Photoinduced Borylation for the Synthesis of Organoboron Compounds

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…Pd/SiC composites prepared on hierarchical SiC nanowires have also been proposed as effective photocatalysts for the borylation of aryl halides under mild conditions and upon visible-light irradiation . Once again these authors have shown the potentiality of the photogenerated electrons on SiC and their subsequent transfer to supported metal nanoparticles for promoting the C–X bond cleavage under milder operational conditions compared to thermal protocols.…”

Section: Catalytic Applicationsmentioning

confidence: 99%

Porous Silicon Carbide (SiC): A Chance for Improving Catalysts or Just Another Active-Phase Carrier?

et al. 2021

View full text Add to dashboard Cite

There is an obvious gap between efforts dedicated to the control of chemicophysical and morphological properties of catalyst active phases and the attention paid to the search of new materials to be employed as functional carriers in the upgrading of heterogeneous catalysts. Economic constraints and common habits in preparing heterogeneous catalysts have narrowed the selection of active-phase carriers to a handful of materials: oxide-based ceramics (e.g. Al2O3, SiO2, TiO2, and aluminosilicates–zeolites) and carbon. However, these carriers occasionally face chemicophysical constraints that limit their application in catalysis. For instance, oxides are easily corroded by acids or bases, and carbon is not resistant to oxidation. Therefore, these carriers cannot be recycled. Moreover, the poor thermal conductivity of metal oxide carriers often translates into permanent alterations of the catalyst active sites (i.e. metal active-phase sintering) that compromise the catalyst performance and its lifetime on run. Therefore, the development of new carriers for the design and synthesis of advanced functional catalytic materials and processes is an urgent priority for the heterogeneous catalysis of the future. Silicon carbide (SiC) is a non-oxide semiconductor with unique chemicophysical properties that make it highly attractive in several branches of catalysis. Accordingly, the past decade has witnessed a large increase of reports dedicated to the design of SiC-based catalysts, also in light of a steadily growing portfolio of porous SiC materials covering a wide range of well-controlled pore structure and surface properties. This review article provides a comprehensive overview on the synthesis and use of macro/mesoporous SiC materials in catalysis, stressing their unique features for the design of efficient, cost-effective, and easy to scale-up heterogeneous catalysts, outlining their success where other and more classical oxide-based supports failed. All applications of SiC in catalysis will be reviewed from the perspective of a given chemical reaction, highlighting all improvements rising from the use of SiC in terms of activity, selectivity, and process sustainability. We feel that the experienced viewpoint of SiC-based catalyst producers and end users (these authors) and their critical presentation of a comprehensive overview on the applications of SiC in catalysis will help the readership to create its own opinion on the central role of SiC for the future of heterogeneous catalysis.

show abstract

“…15 According to the general procedure, the reaction of 1-(4-acetylbenzoyl)piperidine-2,6-dione (25.9 mg, 0.1 mmol, 1.0 equiv), bis(pinacolato)diboron (50.8 mg, 0.2 mmol, 2.0 equiv), Rh(PPh 3 ) 3 Cl (1.9 mg, 0.002 mmol, 0.02 equiv) in toluene (0.5 mL) for 15 h at 160 °C, afforded after workup and chromatography the title compound in 83% yield (20.4 2-(4-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3h, Figure 2). 24 According to the general procedure, the reaction of 1-(4-fluorobenzoyl)piperidine-2,6-dione (23.5 mg, 0.1 mmol, 1.0 equiv), bis(pinacolato)diboron (50.8 mg, 0.2 mmol, 2.0 equiv), Rh(PPh 3 ) 3 Cl (1.9 mg, 0.002 mmol, 0.02 equiv) in toluene (0.5 mL) for 15 h at 160 °C, afforded after workup and chromatography the title compound in 98% yield (21.7 mg). White solid.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Rh-Catalyzed Base-Free Decarbonylative Borylation of Twisted Amides

et al. 2020

View full text Add to dashboard Cite

We report the rhodium-catalyzed base-free decarbonylative borylation of twisted amides. The synthesis of versatile arylboronate esters from aryl twisted amides is achieved via decarbonylative rhodium(I) catalysis and highly selective N–C(O) insertion. The method is notable for a very practical, additive-free Rh(I) catalyst system. The method shows broad functional group tolerance and excellent substrate scope, including site-selective decarbonylative borylation/Heck cross-coupling via divergent N–C/C–Br cleavage and late-stage pharmaceutical borylation.

show abstract

Photocatalytic C–X borylation of aryl halides by hierarchical SiC nanowire-supported Pd nanoparticles

Cited by 16 publications

References 58 publications

Photoinduced Borylation for the Synthesis of Organoboron Compounds

Photoinduced Borylation for the Synthesis of Organoboron Compounds

Porous Silicon Carbide (SiC): A Chance for Improving Catalysts or Just Another Active-Phase Carrier?

Rh-Catalyzed Base-Free Decarbonylative Borylation of Twisted Amides

Contact Info

Product

Resources

About