CdS Quantum Dots for Metallaphotoredox-Enabled Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides

被引:17
作者
Mouat, Julianna M. [2 ]
Widness, Jonas K. [2 ]
Enny, Daniel G. [2 ]
Meidenbauer, Mahilet T. [1 ]
Awan, Farwa [3 ]
Krauss, Todd D. [3 ,4 ]
Weix, Daniel J. [2 ]
机构
[1] Univ Rochester, Mat Sci Program, Rochester, NY 14627 USA
[2] Univ Wisconsin Madison, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA
[3] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
[4] Univ Rochester, Inst Opt, Rochester, NY 14627 USA
关键词
quantum dot; nanoplatelet; nickel; cross-electrophile coupling; C-C bond formation; photochemistry; LIGHT PHOTOREDOX CATALYSIS; LIGAND-EXCHANGE; PHOTOPHYSICAL PROPERTIES; TRIETHANOLAMINE TEA; ENERGY-TRANSFER; METAL; PHOTOCATALYSIS; NANOCRYSTALS; COMPLEX; SURFACE;
D O I
10.1021/acscatal.3c01984
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Semiconductor quantum dots (QDs) offer many advantagesas photocatalystsfor synthetic photoredox catalysis, but no reports have explored theuse of QDs with nickel catalysts for C-C bond formation. Weshow here that 5.7 nm CdS QDs are robust photocatalysts for photoredox-promotedcross-electrophile coupling (turnover number (TON) up to 40,000).These conditions can be utilized on a small scale (96-well plate)or adapted to flow. NMR studies show that triethanolamine (TEOA)-cappedQDs are the active catalyst and that TEOA can displace native phosphonateand carboxylate ligands, demonstrating the importance of the QD surfacechemistry.
引用
收藏
页码:9018 / 9024
页数:7
相关论文
共 81 条
  • [1] Semiconductor clusters, nanocrystals, and quantum dots
    Alivisatos, AP
    [J]. SCIENCE, 1996, 271 (5251) : 933 - 937
  • [2] Ligand Exchange and the Stoichiometry of Metal Chalcogenide Nanocrystals: Spectroscopic Observation of Facile Metal-Carboxylate Displacement and Binding
    Anderson, Nicholas C.
    Hendricks, Mark P.
    Choi, Joshua J.
    Owen, Jonathan S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (49) : 18536 - 18548
  • [3] Quantum Dot-Sensitized Photoreduction of CO2 in Water with Turnover Number > 80,000
    Arcudi, Francesca
    Dordevic, Luka
    Nagasing, Benjamin
    Stupp, Samuel, I
    Weiss, Emily A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (43) : 18131 - 18138
  • [4] Triethanolamine-capped CdSe quantum dots as fluorescent sensors for reciprocal recognition of mercury (II) and iodide in aqueous solution
    Bin Shang, Zhuo
    Wang, Yu
    Jin, Wei Jun
    [J]. TALANTA, 2009, 78 (02) : 364 - 369
  • [5] General and Efficient C-C Bond Forming Photoredox Catalysis with Semiconductor Quantum Dots
    Caputo, Jill A.
    Frenette, Leah C.
    Zhao, Norman
    Sowers, Kelly L.
    Krauss, Todd D.
    Weix, Daniel J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (12) : 4250 - 4253
  • [6] Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis
    Chan, Amy Y.
    Perry, Ian B.
    Bissonnette, Noah B.
    Buksh, Benito F.
    Edwards, Grant A.
    Frye, Lucas, I
    Garry, Olivia L.
    Lavagnino, Marissa N.
    Li, Beryl X.
    Liang, Yufan
    Mao, Edna
    Millet, Agustin
    Oakley, James, V
    Reed, Nicholas L.
    Sakai, Holt A.
    Seath, Ciaran P.
    MacMillan, David W. C.
    [J]. CHEMICAL REVIEWS, 2022, 122 (02) : 1485 - 1542
  • [7] Ligand removal from CdS quantum dots for enhanced photocatalytic H2 generation in pH neutral water
    Chang, Christina M.
    Orchard, Katherine L.
    Martindale, Benjamin C. M.
    Reisner, Erwin
    [J]. JOURNAL OF MATERIALS CHEMISTRY A, 2016, 4 (08) : 2856 - 2862
  • [8] Redox Photocatalysis with Water-Soluble Core Shell CdSe-ZnS Quantum Dots
    Chauvire, Timothee
    Mouesca, Jean-Marie
    Gasparutto, Didier
    Ravanat, Jean-Luc
    Lebrun, Colette
    Gromova, Marina
    Jouneau, Pierre-Henri
    Chauvin, Jerome
    Gambarelli, Serge
    Maurel, Vincent
    [J]. JOURNAL OF PHYSICAL CHEMISTRY C, 2015, 119 (31) : 17857 - 17866
  • [9] Visible-light-induced denitrogenative phosphorylation of benzotriazinones: a metal- and additive-free method for accessing ortho-phosphorylated benzamide derivatives
    Chen, Fushan
    Hu, Shanshan
    Li, Sipei
    Tang, Guo
    Zhao, Yufen
    [J]. GREEN CHEMISTRY, 2021, 23 (01) : 296 - 301
  • [10] Tight Binding of Carboxylate, Phosphonate, and Carbamate Anions to Stoichiometric CdSe Nanocrystals
    Chen, Peter E.
    Anderson, Nicholas C.
    Norman, Zachariah M.
    Owen, Jonathan S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (08) : 3227 - 3236