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Chemical Structure| 870717-91-2 Chemical Structure| 870717-91-2

Structure of 870717-91-2

Chemical Structure| 870717-91-2

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Product Citations

Product Citations

Gruszczyński, Marcin ; Lewandowski, Dariusz ; Kuciński, Krzysztof ; Kubicki, Maciej ; Hreczycho, Grzegorz ;

Abstract: Nickel catalysis provides opportunities to modulate reaction pathways through changes in the coordination environment, yet strategies to deliberately redirect nickel reactivity remain limited. Here we show that ligand exchange at nickel allows a single catalytic system to produce different products from the same alkyne substrates. Aminophosphine-supported nickel catalysts promote selective hydroboration in the presence of pinacolborane, which functions both as a boron source and a reaction activator. The addition of forms a distinct ligand-coordinated nickel species that suppresses hydroboration and directs the reaction toward enyne formation. Our further studies identify coordination as a key step that directs the catalytic cycle, illustrating how simple additives can influence reaction outcomes. These results offer a straightforward strategy to access divergent reactivity in nickel catalysis and provide insight into the factors controlling catalytic pathway selection.

Keywords: Alkynes ; Nickel catalysis ; Ligand effects ; Hydroboration ; Enynes

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Product Details of [ 870717-91-2 ]

CAS No. :870717-91-2
Formula : C16H23BO2
M.W : 258.16
SMILES Code : CC1(C)C(C)(C)OB(/C=C/C2=CC=C(CC)C=C2)O1
English Name :(E)-2-(4-Ethylstyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
MDL No. :MFCD08276837

Safety of [ 870717-91-2 ]

Application In Synthesis of [ 870717-91-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 870717-91-2 ]

[ 870717-91-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 124-38-9 ]
  • [ 870717-91-2 ]
  • [ 120680-98-0 ]
YieldReaction ConditionsOperation in experiment
85% With potassium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
85% With potassium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 70℃; for 24h; Sealed tube; Schlenk technique; 24 Example 24 In the glove box, add trans-2-(4-ethylphenyl)vinylboronic acid pinacol ester (1mmol, 258.2mg) into a 50mL Schlenk bottle equipped with a stir bar.Potassium methoxide (2mmol, 2 equivalents, 140.2mg), CuCl (0.03mmol, 0.03 equivalents, 3.0mg), 5mL solvent N,N-dimethylacetamide.Take out the capped Schlenk bottle from the glove box, fully ventilate, fill the reaction system with carbon dioxide and seal it, and then stir the reaction mixture at 70°C for 24 hours.After cooling to room temperature, add 1mol/L hydrochloric acid to acidify, and extract with ethyl acetate, and then wash with brine once.The organic phase was collected and concentrated in vacuo. The liquid mixture was dropped on a silica gel column and purified by column chromatography. The developing solvent was petroleum ether/ethyl acetate.The desired product trans-3-(4-ethylphenyl)acrylic acid was obtained with a yield of 85%.
 

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