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Chemical Structure| 1294009-26-9 Chemical Structure| 1294009-26-9

Structure of 1294009-26-9

Chemical Structure| 1294009-26-9

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Product Citations

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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

Purchased from AmBeed: ; ; ; ;

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Product Details of [ 1294009-26-9 ]

CAS No. :1294009-26-9
Formula : C15H21BO2
M.W : 244.14
SMILES Code : CC1=CC=CC=C1/C=C/B2OC(C)(C)C(C)(C)O2
English Name :(E)-4,4,5,5-Tetramethyl-2-(2-methylstyryl)-1,3,2-dioxaborolane
MDL No. :MFCD19703869

Safety of [ 1294009-26-9 ]

Application In Synthesis of [ 1294009-26-9 ]

* 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 [ 1294009-26-9 ]

[ 1294009-26-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 766-47-2 ]
  • [ 73183-34-3 ]
  • [ 1294009-26-9 ]
YieldReaction ConditionsOperation in experiment
89% With [Cu(phen)(xantphosTEPD)]PF6; potassium carbonate In water; acetonitrile at 20℃; for 7h; Sealed tube; Inert atmosphere; Irradiation; diastereoselective reaction;
85% With copper(I) oxide supported on ceria nanoparticle In ethanol at 90℃; for 1h; Inert atmosphere; Schlenk technique; Substrate scope investigations with the Cu1-O(I)/CeO2 catalyst General procedure: In a typical procedure, B2Pin2 (0.7 mmol, 177.4 mg) and Cu1-O(I)/CeO2 (Cu = 0.5 mol %, 7.6 mg) were placed in adried Schlenk tube equipped with a stir bar. After evacuation under vacuum and flushing with N2 for three times,alkyne substrate (0.5 mmol) and ethanol (2.0 mL) were injected under the atmosphere of N2. The mixture wasultrasonically vibrated to form a uniform suspension and then stirred at 90oC for 1.0 h. Upon completion, the reactionmixture was analyzed by GC-MS to determine the selectivity of vinylboronate products. To determine the isolatedyield of the target product, the reaction mixture was centrifuged to remove the catalyst, and the supernate wasconcentrated in vacuum. The residue was purified by flash column chromatography on silica gel with petroleumether/ethyl acetate as eluent.
85% With tetrabutylammonium phosphomolybdate; sodium methylate In ethanol at 25℃; for 18h;
84% With potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In water; acetonitrile at 25℃; for 0.333333h; stereoselective reaction;
84% With water; potassium carbonate; 6Cu(1+)*3C20H14N6O4(2-) In acetonitrile at 25℃; for 0.333333h; stereoselective reaction;
75% Stage #1: bis(pinacol)diborane With [1,3-bis(1-adamantyl)imidazolidin-2-yl]chloro-copper; sodium t-butanolate In tetrahydrofuran at 22℃; for 0.5h; Inert atmosphere; Stage #2: 1-ethynyl-2-methylbenzene With methanol In tetrahydrofuran at 22℃; for 12h; Inert atmosphere; regioselective reaction;
73% With tetrabutylammonium tetrafluoroborate In methanol at 20℃; Electrochemical reaction;
73% With tetrabutylammonium tetrafluoroborate In methanol
70% With [bis(acetoxy)iodo]benzene; sodium t-butanolate In ethanol at 20℃; for 12h; regioselective reaction;
Stage #1: bis(pinacol)diborane With copper; sodium methylate In 1,4-dioxane; ethanol for 0.5h; Inert atmosphere; Sealed tube; Stage #2: 1-ethynyl-2-methylbenzene In 1,4-dioxane; ethanol at 60℃; Inert atmosphere;
With methanol; DPEPhos; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Glovebox; Sealed tube;
95 % With ethanol at 30℃; Autoclave; Inert atmosphere;
88 % With methanol; N-propyl-N-(2-(pyridin-2-ylamino)phenyl)formamide In tetrahydrofuran at 60℃; Schlenk technique; stereoselective reaction;
With sodium methylate; copper In ethanol at 20℃;

References: [1]Zhong, Mingbing; Gagné, Yohann; Hope, Taylor O.; Pannecoucke, Xavier; Frenette, Mathieu; Jubault, Philippe; Poisson, Thomas [Angewandte Chemie - International Edition, 2021, vol. 60, # 26, p. 14498 - 14503][Angew. Chem., 2021, vol. 133, # 26, p. 14619 - 14624].
[2]Zhang, Jian; Wang, Ziyun; Chen, Wenxing; Xiong, Yu; Cheong, Weng-Chon; Zheng, Lirong; Yan, Wensheng; Gu, Lin; Chen, Chen; Peng, Qing; Hu; Wang, Dingsheng; Li, Yadong [Chem, 2020, vol. 6, # 3, p. 725 - 737].
[3]Peng, Dong; Sun, Jiayi; Huang, Yun; Zeng, Xianghua; Wei, Yongge [Journal of Organic Chemistry, 2026, vol. 91, # 4, p. 1758 - 1766].
[4]Wei, Rong-Jia; You, Pei-Ye; Duan, Haiyan; Xie, Mo; Xia, Ri-Qin; Chen, Xu; Zhao, Xiaoxu; Ning, Guo-Hong; Cooper, Andrew I.; Li, Dan [Journal of the American Chemical Society, 2022, vol. 144, # 38, p. 17487 - 17495].
[5]Wei, Rong-Jia; You, Pei-Ye; Duan, Haiyan; Xie, Mo; Xia, Ri-Qin; Chen, Xu; Zhao, Xiaoxu; Ning, Guo-Hong; Cooper, Andrew I.; Li, Dan [Journal of the American Chemical Society, 2022, vol. 144, # 38, p. 17487 - 17495].
[6]Jang, Hwanjong; Zhugralin, Adil R.; Lee, Yunmi; Hoveyda, Amir H. [Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7859 - 7871].
[7]Aelterman, Maude; Sayes, Morgane; Jubault, Philippe; Poisson, Thomas [Chemistry - A European Journal, 2021, vol. 27, # 32, p. 8277 - 8282].
[8]Xia, Ming; Mutailipu, Miriding; Li, Fuming; Yang, Zhihua; Pan, Shilie [Chemistry - A European Journal, 2021, vol. 27, # 38, p. 9753 - 9757].
[9]Chen, Suyuan; Yang, Lu; Yi, Dong; Fu, Qiang; Zhang, Zhijie; Liang, Wu; Zhang, Qiang; Ji, Jianxin; Wei, Wei [RSC Advances, 2017, vol. 7, # 42, p. 26070 - 26073].
[10]Liu, Shiwen; Zeng, Xiaojun; Hammond, Gerald B.; Xu, Bo [Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3667 - 3671].
[11]Liu, Yanyao; Ni, Dongshun; Brown, M. Kevin [Journal of the American Chemical Society, 2022, vol. 144, # 41, p. 18790 - 18796].
[12]Xu, Hang; Yamaguchi, Sho; Mitsudome, Takato; Mizugaki, Tomoo [Organic and Biomolecular Chemistry, 2022, vol. 21, # 7, p. 1404 - 1410].
[13]Tao, Sheng; Wang, Yang; Pan, Qianxiu; Zhao, Jixing; Bu, Qingqing; Chen, Fei; Liu, Jichang; Dai, Bin; Wei, Donghui; Liu, Ning [Green Chemistry, 2023, vol. 25, # 17, p. 6704 - 6716].
[14]Manna, Samir; Paul, Swagata; Kong, Wang-Yeuk; Aich, Debasis; Sahoo, Rupam; Tantillo, Dean J.; Panda, Santanu [Angewandte Chemie - International Edition, 2023, vol. 62, # 38][Angew. Chem., 2023, vol. 135, # 62].
  • 2
  • [ 766-47-2 ]
  • [ 73183-34-3 ]
  • [ 1294009-26-9 ]
  • [ 2169318-18-5 ]
YieldReaction ConditionsOperation in experiment
51% With NaOC(CH3)3; CH3OH In tetrahydrofuran 1.0 mol% Cu-complex, alkyne, diborane, NaOC(CH3)3, CH3OH, THF, -15°C, 24 h, N2 atm.; 70:30 ratio of isomers;
Stage #1: bis(pinacol)diborane With C178H184ClCuN2O33; potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-ethynyl-2-methylbenzene In tetrahydrofuran; methanol at -20℃; for 16h; regioselective reaction;
  • 3
  • [ 766-47-2 ]
  • [ 25015-63-8 ]
  • [ 1294009-26-9 ]
  • [ 1361046-87-8 ]
YieldReaction ConditionsOperation in experiment
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine; tricyclohexylphosphine In tetrahydrofuran at 25℃; for 4h; Inert atmosphere; regioselective reaction;
1: 71 %Spectr. 2: 7 %Spectr. With 2Fe(1+)*9CO In toluene at 100℃; for 24h; Inert atmosphere;
  • 4
  • [ CAS Unavailable ]
  • [ 1294009-26-9 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
79% In tetrahydrofuran; water at 20℃;
  • 5
  • [ 766-47-2 ]
  • [ 25015-63-8 ]
  • [ 1294009-26-9 ]
YieldReaction ConditionsOperation in experiment
96% With lithium triethylborohydride; C76H65Cl2CoN3 In neat (no solvent) at 80℃; for 18h; Schlenk technique; Inert atmosphere;
90% With LDBBA In neat (no solvent) at 50℃; for 12h; Inert atmosphere;
86% With [RuHCl(CO)(PPh3)3] In toluene at 50℃; for 16h; Inert atmosphere;
85% In neat (no solvent) at 110℃; for 12h; Inert atmosphere;
80% With dibutylmagnesium In n-heptane; toluene at 80℃; for 18h; Inert atmosphere; regioselective reaction;
76% With Lithium 1,1,1,3,3,3-hexamethyldisilazide In toluene at 100℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;
In neat (no solvent) at 110℃; for 14h; Inert atmosphere;
64 %Spectr. With MIL-53(Al) metal-organic framework-CoH In neat (no solvent) at 90℃; for 22h;
at 215℃; for 0.3h; Schlenk technique; Inert atmosphere; Microwave irradiation;
59 %Chromat. With sodium triethylborohydride for 1h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction; 2.2. General procedure of NaHBEt3-catalysed hydroboration General procedure: 1.0 mmol of alkyne, 0.1 mL of decane and 1.1 mmol of pinacolborane,were placed in previously evacuated Schlenk bomb flask fitted witha plug valve. A reference sample was taken. Next, 0.1 mL of 1 M solutionof NaHBEt3 (0.1 mmol) in toluene was added, reaction vessel was closedand heated at 60 C with stirring. After specified time, reaction mixturewas cooled down to the room temperature and analysed using GC andGC-MS. Products of hydroboration were isolated by extraction with 1mL of DCM followed by column chromatography of concentrated extract(SiO2, hexane/Et2O, 98:2).
86 % With C31H50NO2Si2Y In toluene at 110℃; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;
74 % With [Mn(2,6-bis(diisopropylphosphinomethyl)pyridine)Cl2]10 In tetrahydrofuran at 30℃;
80 % With manganese(II) bromide; sodium triethylborohydride In hexane at 70℃; Inert atmosphere; Sealed tube; chemoselective reaction;
58 % With 3,3'-bis[(diphenylphosphino)methyl]-2,2'-bipyridine; cobalt(II) aceylacetonate In ethyl acetate at 25℃; Schlenk technique;
With Triethoxysilane In 1,4-dioxane at 80℃; for 24h; regioselective reaction;

References: [1]Bołt, Małgorzata; Żak, Patrycja [RSC Advances, 2022, vol. 12, # 29, p. 18572 - 18577].
[2]Jaladi, Ashok Kumar; Kim, Hanbi; Lee, Ji Hye; Shin, Won Kyu; Hwang, Hyonseok; An, Duk Keun [New Journal of Chemistry, 2019, vol. 43, # 42, p. 16524 - 16529].
[3]Yasu, Yusuke; Koike, Takashi; Akita, Munetaka [Chemical Communications, 2013, vol. 49, # 20, p. 2037 - 2039].
[4]Jaladi, Ashok Kumar; Choi, Hyeon Seong; An, Duk Keun [New Journal of Chemistry, 2020, vol. 44, # 32, p. 13626 - 13632].
[5]Magre, Marc; Maity, Bholanath; Falconnet, Alban; Cavallo, Luigi; Rueping, Magnus [Angewandte Chemie - International Edition, 2019, vol. 58, # 21, p. 7025 - 7029][Angew. Chem., 2019, vol. 131, # 21, p. 7099 - 7103,5].
[6]Liu, Jichao; Wu, Caiyan; Hu, Tinghui; Yang, Wei; Xie, Yaoyao; Shi, Yinyin; Liu, Qianrui; Shao, Yinlin; Zhang, Fangjun [Journal of Organic Chemistry, 2022, vol. 87, # 5, p. 3442 - 3452].
[7]Carreras, Javier; Caballero, Ana; Pérez, Pedro J. [Angewandte Chemie - International Edition, 2018, vol. 57, # 9, p. 2334 - 2338][Angew. Chem., 2018, vol. 130, p. 2358 - 2362,5].
[8]Feng, Xuanyu; Ji, Pengfei; Li, Zhe; Drake, Tasha; Oliveres, Pau; Chen, Emily Y.; Song, Yang; Wang, Cheng; Lin, Wenbin [ACS Catalysis, 2019, vol. 9, # 4, p. 3327 - 3337].
[9]Altarejos, Julia; Sucunza, David; Vaquero, Juan J.; Carreras, Javier [Organic Letters, 2021, vol. 23, # 15, p. 6174 - 6178].
[10]Maj, Anna M.; Szarłan, Bartłomiej; Pawluć, Piotr; Zaranek, Maciej [Polyhedron, 2022, vol. 223].
[11]Iqbal, Muhammad Asif; Yan, Xiangqian; Li, Ruoling; Zhijia, Fu; Zhang, Shaowen; Li, Xiaofang [New Journal of Chemistry, 2024, vol. 48, # 7, p. 3149 - 3155].
[12]Duran Arroyo, Victor; Arevalo, Rebeca [RSC Advances, 2024, vol. 14, # 8, p. 5514 - 5523].
[13]Pawar, Rameshwar B.; Karmur, Mital H.; Punji, Benudhar [Chemistry - An Asian Journal, 2024, vol. 19, # 9].
[14]Li, Zheng; Zhao, Jiangui; Xue, Weichao; Tang, Juan; Li, Shun; Ge, Yicen; Xu, Jiaqi; Zheng, Xueli; Li, Ruixiang; Chen, Hua; Fu, Haiyan [Organic and Biomolecular Chemistry, 2024, vol. 22, # 22, p. 4455 - 4460].
[15]Kaur, Harleen; Ahuja, Himani; Arevalo, Rebeca [ACS Catalysis, 2025, vol. 15, # 2, p. 976 - 981].
  • 6
  • [ 1294009-26-9 ]
  • [ 1357615-52-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran; water / 20 °C 2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate / methanol / 5 h / 20 °C / Inert atmosphere; Irradiation; Schlenk technique
  • 7
  • [ 1294009-26-9 ]
  • [ 1505469-63-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
80% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 95℃; Inert atmosphere; Schlenk technique;
  • 8
  • [ 1294009-26-9 ]
  • [ 1505469-66-8 ]
  • [ 1505469-82-8 ]
YieldReaction ConditionsOperation in experiment
85% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 95℃; Inert atmosphere; Schlenk technique;
  • 9
  • [ 7515-27-7 ]
  • [ 73183-34-3 ]
  • [ 1294009-26-9 ]
YieldReaction ConditionsOperation in experiment
74% With copper(l) iodide; lithium methanolate; bis[2-(diphenylphosphino)phenyl] ether In dimethyl sulfoxide at 50℃; for 16h; General Procedure. General procedure: Phenylpropiolic acid (439 mg, 3.0 mmol), B2pin2 (763 mg, 3.0 mmol), lithium methoxide (23 mg, 0.6 mmol), copper iodide (57 mg, 0.3 mmol), and Dpe-Phos (324 mg, 0.6 mmol) were added to a vial containing DMSO (5 mL). The suspension was stirred for 16 h at 50 °C. The reaction was monitored by TLC, and after the completion of the reaction, the reaction mass was cooled to 25-28 °C and quenched into a mixture of 50 mL of water and 50 mL of ethyl acetate. The ethyl acetate layer was washed with water (2 × 25 mL), brine (2 × 25 mL), and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography (hexane:EtOAc = 9.5:0.5).
  • 10
  • [ 3066-75-9 ]
  • [ 1294009-26-9 ]
  • [ 2033124-07-9 ]
YieldReaction ConditionsOperation in experiment
76% With Walphos SL-W001-1; copper(l) chloride; lithium tert-butoxide In diethyl ether at 40℃; for 12h; Schlenk technique; enantioselective reaction;
 

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