Nickel-catalysed P–C bond formation via P–H/C–CN cross coupling reactions

Zhang, Jishu; Chen, Tieqiao; Yang, Jia; Han, Li‐Biao

doi:10.1039/c5cc01182e

Cited by 103 publications

(51 citation statements)

References 52 publications

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“…Working with the orthogonal two-phosphorylase cascade reactions, other researchers have applied enzymatic isomerization of the fructose released from sucrose for the in situ formation of glucose as acceptor substrate. The glucose was then to be glucosylated from Glc1-P. Well-studied examples are the biosynthesis of laminaribiose, [43] cellobiose, [34,35] and , -trehalose [37,38] from sucrose. External addition of glucose detracts from the atom economy of the overall reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Orthogonal two-enzyme phosphorylase cascades have been reported for the synthesis of disaccharides (e.g., cellobiose, [33][34][35] , -trehalose, [36][37][38][39] laminaribiose, [40][41][42][43] kojibiose, [44,45] nigerose [46] ), oligo-, and polysaccharides (e.g., -glucans, [47,48] amylose [49,50] ). Sucrose or starch was the donor substrate to fuel the phosphate/ Glc 1-P shuttle.…”

Section: Introductionmentioning

confidence: 99%

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Three‐Enzyme Phosphorylase Cascade for Integrated Production of Short‐Chain Cellodextrins

Zhong

Nidetzky

2019

Biotechnology Journal

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Cellodextrins are linear β‐1,4‐gluco‐oligosaccharides that are soluble in water up to a degree of polymerization (DP) of ≈6. Soluble cellodextrins have promising applications as nutritional ingredients. A DP‐controlled, bottom‐up synthesis from expedient substrates is desired for their bulk production. Here, a three‐enzyme glycoside phosphorylase cascade is developed for the conversion of sucrose and glucose into short‐chain (soluble) cellodextrins (DP range 3–6). The cascade reaction involves iterative β‐1,4‐glucosylation of glucose from α‐glucose 1‐phosphate (αGlc1‐P) donor that is formed in situ from sucrose and phosphate. With final concentration and yield of the soluble cellodextrins set as targets for biocatalytic synthesis, three major factors of reaction efficiency are identified and partly optimized: the ratio of enzyme activity, the ratio of sucrose and glucose, and the phosphate concentration used. The efficient use of the phosphate/αGlc1‐P shuttle for cellodextrin production is demonstrated and the soluble product at 40 g L−1 is obtained under near‐complete utilization of the donor substrate offered (88 mol% from 200 mm sucrose). The productivity is 16 g (L h)−1. Through a simple two‐step route, the soluble cellodextrins are recovered from the reaction mixture in ≥95% purity and ≈92% yield. Overall, this study provides the basis for their integrated production.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Three‐Enzyme Phosphorylase Cascade for Integrated Production of Short‐Chain Cellodextrins

Zhong

Nidetzky

2019

Biotechnology Journal

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“…This etching strategy is also applied in other Rh-based hollow nanostructures such as CuÀRh nanooctahedral frames, RhCu 3D nanoframes and PdÀRh nanoboxes. [46,69,70] Epitaxial growth of highly ordered Rh island nanocrystals with a controlled size, orientation, surface structure and interface was realized by Sneed et al who also applied Pd nanocrytals as a substrate. [71] Instead of following a layered growth mode, the Rh islands were observed to take on a distinct shape due to the iodide-mediated overgrowth.…”

Section: Template-assisted Growthmentioning

confidence: 99%

“…[44,45] Rh is a 4d transition metal on the top rank of the rarest and the most expensive Pt-group metals (PGMs). [46] Rh possesses partially filled 4d electrons which enable the moderate adsorption of reactants and thus promote the formation of intermediates. [47] Besides, the resistance to high temperature, oxidation, and corrosion renders the Rh-based materials desired industrial catalysts for a variety of heterogeneous catalysis such as hydrogenation, hydrogen production, oxidation, etc.…”

Section: Introductionmentioning

confidence: 99%

Rh‐Based Nanocatalysts for Heterogeneous Reactions

Luo

Peng

et al. 2018

ChemNanoMat

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Rhodium (Rh) is well‐known for its catalytic application in diverse industrial reactions such as methane conversion, hydrogen generation, and olefin hydroformylation. Compared to homogeneous catalysts, heterogeneous Rh‐based nanocatalysts are facilely separated and collected after reactions, thus being more compatible for industrialization. To this end, the development of active and stable heterogeneous Rh‐based catalysts has received everlasting interest. In this review, we focus on the synthesis and catalytic application of Rh‐based nanocatalysts for heterogeneous catalysis. Recent efforts in the design and fabrication of Rh‐based nanocatalysts are highlighted. Various synthetic strategies and protocols for shape‐controlled synthesis of Rh‐based nanocrystals and supported Rh‐based nanocatalysts are overviewed. In addition, we introduce methane conversion, hydrogen generation, and olefin hydroformylation as three typical catalytic applications of the Rh‐based nanocatalysts, and provide insights into the catalytic mechanisms involved. The remaining challenges and future prospects for the Rh‐based heterogeneous nanocatalysts are also discussed. This review offers a guideline for future research on Rh‐based nanocatalysts for heterogeneous catalysis.

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“…Chatani demonstrated a Rh I ‐catalyzed silylation reaction of aryl cyanides with hexamethyldisilane involving the cleavage of Ar–CN and Si–Si bonds (Scheme b) . Yang established a phosphination of aryl cyanides with Me 3 SiPPh 2 through Ni‐catalyzed Ar–CN bond cleavage for the synthesis of various diphenylphosphoryl compounds (Scheme c) . Tobisu and Chatani also disclosed the borylation of aryl cyanides with diboron in the presence of a Rh I /Xantphos catalyst and DABCO to afford a variety of arylboronic esters (Scheme d) …”

Section: Introductionmentioning

confidence: 99%

Decyanative Cross‐Coupling of Cyanopyrimidines with O‐, S‐, and N‐Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

et al. 2019

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The transition metal‐free cross‐coupling reactions of cyanopyrimidines with aliphatic alcohols, thiols (or S‐alkylisothiourea salts) and amines, giving the corresponding alkoxylpyrimidines, aminopyrimidines, and alkylthiopyrimidines, are reported. Preliminary mechanistic studies reveal that it probably involves a sequential nucleophilic addition‐intramolecular rearrangement process, which is promoted by an intramolecular N–H···N five‐membered hydrogen bonding interaction. The presence of a nitrogen atom next to the cyano group is indispensable. The wide substrate scope with excellent yields makes cyanopyrimidines a promising alternative substrate class to the frequently used pyrimidines halides for the formation of C–O, C–S, and C–N bonds through the decyanative cross‐coupling reaction.

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Nickel-catalysed P–C bond formation via P–H/C–CN cross coupling reactions

Cited by 103 publications

References 52 publications

Three‐Enzyme Phosphorylase Cascade for Integrated Production of Short‐Chain Cellodextrins

Three‐Enzyme Phosphorylase Cascade for Integrated Production of Short‐Chain Cellodextrins

Rh‐Based Nanocatalysts for Heterogeneous Reactions

Decyanative Cross‐Coupling of Cyanopyrimidines with O‐, S‐, and N‐Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

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