Selective photocatalytic C–C bond cleavage under ambient conditions with earth abundant vanadium complexes

Gazi, Sarifuddin; Ng, Wai-Kuen; Ganguly, Rakesh; Moeljadi, Adhitya Mangala Putra; Hirao, Hajime; Soo, Han Sen

doi:10.1039/c5sc02923f

Cited by 153 publications

(143 citation statements)

References 51 publications

(137 reference statements)

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“…[47] The direct CÀCb ond cleavage was confirmed by 13 Ca nd 2 Hi sotope-labeling experiments, during which no scrambling of the benzylic hydrogen atom before or after bond cleavage was observed. [47] The direct CÀCb ond cleavage was confirmed by 13 Ca nd 2 Hi sotope-labeling experiments, during which no scrambling of the benzylic hydrogen atom before or after bond cleavage was observed.…”

Section: V Complexesmentioning

confidence: 84%

“…The Soo group reported aV V -based photocatalyst that cleaved CÀCb onds in aliphatic alcohols with high regioselectivity under visible-light irradiationa nd ambient conditions to generate two valuable products, aryl aldehydes and formate, in moderate to high yields (Scheme 9). [47] The direct CÀCb ond cleavage was confirmed by 13 Ca nd 2 Hi sotope-labeling experiments, during which no scrambling of the benzylic hydrogen atom before or after bond cleavage was observed. The mechanism wasp robed by time-dependent (TD)DFT calculation, which suggested that excitation of the ligand-to-metal chargetransfer (LMCT)band in the alcohol-V V -photocatalyst complex induced hemolytic CÀCb ond cleavage.…”

Section: V Complexesmentioning

confidence: 84%

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Conversion of Lignin Models by Photoredox Catalysis

Zhang

2018

ChemSusChem

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One prominent goal of 21st century research is to develop a sustainable carbon-neutral biorefinery. Lignin is an important component of lignocellulosic biomass; however, it is currently underutilized owing to its highly cross-linked, complex, and randomly polymerized composition, which poses a significant challenge to its depolymerization and valorization. Chemical catalytic approaches based on transition metals represent the primary research area to drive degradation reactions. Recently, alternative photocatalytic strategies that employ sustainable solar energy to initiate the transformation of lignin have started to emerge. This Concept article examines new developments of photocatalyzed reactions and provides insight into C-O and C-C bond-cleavage reactions of lignin models in both homogeneous and heterogeneous systems.

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Section: V Complexesmentioning

confidence: 84%

Section: V Complexesmentioning

confidence: 84%

Conversion of Lignin Models by Photoredox Catalysis

Zhang

2018

ChemSusChem

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“…A 1,4‐hydroquinone/copper nanoparticle catalytic system was used for C α C β bond oxidative cleavage under visible‐light irradiation with low yields of aromatic aldehydes and phenols . Soo and co‐workers reported a more efficient vanadium photocatalyst . The vanadium complex harvested visible light and realized C α C β bond oxidative cleavage.…”

Section: The Challengesmentioning

confidence: 99%

Catalytic Scissoring of Lignin into Aryl Monomers

Wang

2019

Advanced Materials

139

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Lignin is an aromatic polymer, which is the biggest and most sustainable reservoir for aromatics. The selective conversion of lignin polymers into aryl monomers is a promising route to provide aromatics, but it is also a challenging task. Compared to cellulose, lignin remains the most poorly utilized biopolymer due to its complex structure. Although harsh conditions can degrade lignin, the aromatic rings are usually destroyed. This article comprehensively analyzes the challenges facing the scissoring of lignin into aryl monomers and summarizes the recent progress, focusing on the strategies and the catalysts to address the problems. Finally, emphasis is given to the outlook and future directions of this research.

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“…[57,58] While compounds with aromatic substituents show lifetimes below 200 ns with quantum yields < 1%,c omplexes with bulky alkyl substituents (R = adamantyl, tert-butyl) exhibit longer-lived emission with lifetimes and quantum yields of up to 15.1 msa nd 20 %, respectively.M ore recently,h ydrazone-imidate vanadium(V) oxo complexes with luminescence lifetimes of up to 9.9 ns in acetonitrile have been utilized in photocatalysis. [59,60] The exciteds tate was assigned as LMCT (O 2À !V V )v ia density functional theory.…”

Section: Introductionmentioning

confidence: 99%

Photoluminescence of Seven‐Coordinate Zirconium and Hafnium Complexes with 2,2′‐Pyridylpyrrolide Ligands

Zhang

Akhmedov

Petersen

et al. 2019

Chemistry A European J

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Luminescents even-coordinated zirconium and hafniumc omplexes bearing three mono-anionic 2,2'-pyridylpyrrolide ligands and one chloride weres ynthesized.S olidstate structures and the dynamicb ehaviors in solutionw ere probed by X-ray crystallography and variable temperature 1 HNMR experiments, respectively.A bsorption spectroscopy and time-dependent density functional theory( TD-DFT) calculations supported ah ybrid of ligand-to-metal charge transfer( LMCT)/ligand-to-ligand charge transfer (LLCT)f or the visible light absorption band. The complexes ( Me PMP Me ) 3 MCl (M = Zr,H f, Me PMP Me = 3,5-dimethyl-2-(2-pyridyl)pyrrolide) are emissive in solution at room temperature upon irradiation with visible light due to ac ombination of phosphorescence and fluorescencec haracterizedb ye xcited state lifetimes in the msa nd low to sub-ns timescale,r espectively.E lectrochemicale xperiments revealed that the zirconium complex possesses ar eversible redox event under highly reducingcondition (À2.29 Vv s. Fc + /0 ).

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Selective photocatalytic C–C bond cleavage under ambient conditions with earth abundant vanadium complexes

Abstract: Chemoselective aliphatic carbon–carbon bond activation photocatalyzed by vanadium oxo complexes under ambient conditions and visible light.

Cited by 153 publications

References 51 publications

Conversion of Lignin Models by Photoredox Catalysis

Conversion of Lignin Models by Photoredox Catalysis

Catalytic Scissoring of Lignin into Aryl Monomers

Photoluminescence of Seven‐Coordinate Zirconium and Hafnium Complexes with 2,2′‐Pyridylpyrrolide Ligands

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