Arylazo Sulfones as Nonionic Visible-Light Photoacid Generators

被引：9
|
作者：
Di Terlizzi, Lorenzo [1 ]
Martinelli, Angelo [2 ]
Merli, Daniele [2 ]
Protti, Stefano [1 ]
Fagnoni, Maurizio [1 ]
机构：
[1] Univ Pavia, Dept Chem, PhotoGreen Lab, I-27100 Pavia, Italy
[2] Univ Pavia, Dept Chem, I-27100 Pavia, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 10期
关键词：
LASER FLASH-PHOTOLYSIS; CATIONIC-POLYMERIZATION; PHOTOBASE GENERATORS; ORGANIC-SYNTHESIS; RECENT PROGRESS; CATALYST-FREE; I-LINE; TETRAHYDROPYRANYLATION; ALCOHOLS; DEPROTECTION;
D O I：
10.1021/acs.joc.2c01248
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The selective visible-light-driven generation of a weak acid (sulfinic acid, in nitrogen-purged solutions) or a strong acid (sulfonic acid, in oxygen-purged solutions) by using shelf-stable arylazo sulfones was developed. These sulfones were then used for the green, smooth, and efficient photochemical catalytic protection of several (substituted) alcohols (and phenols) as tetrahydropyranyl ethers or acetals.
引用
收藏
页码：6313 / 6321
页数：9
相关论文
共 50 条
  • [1] Synthesis of Aryl Thiocyanates and Aryl Selenocyanates via Visible-Light Activation of Arylazo Sulfones
    Gao, Yu
    Sparascio, Sara
    Di Terlizzi, Lorenzo
    Serra, Massimo
    Yue, Guanglu
    Lu, Yaru
    Fagnoni, Maurizio
    Zhao, Xia
    Protti, Stefano
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (07) : 1082 - 1087
  • [2] Photochemical Michael Addition of Indoles to α,β-Unsaturated Ketones utilizing Arylazo Sulfones as the Photoacid Generators
    Galathri, Eirini M.
    Di Terlizzi, Lorenzo
    Fagnoni, Maurizio
    Protti, Stefano
    Kokotos, Christoforos G.
    CHEMCATCHEM, 2024, 16 (18)
  • [3] Visible-Light Assisted Covalent Surface Functionalization of Reduced Graphene Oxide Nanosheets with Arylazo Sulfones
    Lombardi, Lorenzo
    Kovtun, Alessandro
    Mantovani, Sebastiano
    Bertuzzi, Giulio
    Favaretto, Laura
    Bettini, Cristian
    Palermo, Vincenzo
    Melucci, Manuela
    Bandini, Marco
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (26)
  • [4] ARYLMETHYL SULFONES - A NEW CLASS OF PHOTOACID GENERATORS
    NOVEMBRE, AE
    HANSON, JE
    KOMETANI, JM
    TAI, WW
    REICHMANIS, E
    THOMPSON, LF
    WEST, RJ
    POLYMER ENGINEERING AND SCIENCE, 1992, 32 (20): : 1476 - 1480
  • [5] Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones
    Lian, Chang
    Yue, Guanglu
    Mao, Jinshan
    Liu, Danyang
    Ding, Yi
    Liu, Zerong
    Qiu, Di
    Zhao, Xia
    Lu, Kui
    Fagnoni, Maurizio
    Protti, Stefano
    ORGANIC LETTERS, 2019, 21 (13) : 5187 - 5191
  • [6] Visible-Light Enabled Synthesis of 1-Aryl-3-Sulfonylmethyl-1,2,4-Triazoles by Arylazo Sulfones
    Nicchio, Luca
    Di Terlizzi, Lorenzo
    Fagnoni, Maurizio
    Neuville, Luc
    Protti, Stefano
    Masson, Geraldine
    ADVANCED SYNTHESIS & CATALYSIS, 2024,
  • [7] Photoacid and photobase generators: Arylmethyl sulfones and benzhydrylammonium salts
    Hanson, JE
    Jensen, KH
    Gargiulo, N
    Motta, D
    Pingor, DA
    Novembre, AE
    Mixon, DA
    Kometani, JM
    Knurek, C
    MICROELECTRONICS TECHNOLOGY: POLYMERS FOR ADVANCED IMAGING AND PACKAGING, 1995, 614 : 137 - 148
  • [8] EFFICACY OF VISIBLE-LIGHT GENERATORS WITH CHANGES IN VOLTAGE
    TAKAMIZU, M
    MOORE, BK
    SETCOS, JC
    PHILLIPS, RW
    OPERATIVE DENTISTRY, 1988, 13 (04) : 173 - 180
  • [9] Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones
    Bui, Tien Tan
    Tran, Van Hieu
    Kim, Hee-Kwon
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (02) : 341 - 347
  • [10] Visible-Light-Sensitive Sulfonium Photoacid Generators Bearing a Ferrocenyl Chromophore
    Takahashi, Yukihiro
    Kodama, Shintaro
    Ishii, Youichi
    ORGANOMETALLICS, 2018, 37 (11) : 1649 - 1651
12345