Synthesis of sulfinamides via photocatalytic alkylation or arylation of sulfinylamine

被引:8
|
作者
Yan, Ming [1 ,2 ]
Wang, Si-fan [1 ,2 ]
Zhang, Yong-po [1 ]
Zhao, Jin-zhong [1 ]
Tang, Zhuo [2 ]
Li, Guang-xun [2 ]
机构
[1] Shanxi Agr Univ, Dept Basic Sci, Taigu 030800, Shanxi, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Sichuan, Peoples R China
基金
中国科学院西部之光基金;
关键词
ONE-POT; TERT-BUTANESULFINAMIDES; ASYMMETRIC OXIDATION; SULFUR-DIOXIDE; DABSO; PHARMACOPHORES; 3-COMPONENT; REAGENTS; DESIGN;
D O I
10.1039/d3ob01782f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sulfinamides are a versatile class of compounds that find applications in both organic synthesis and pharmaceuticals. Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. Commercially available potassium trifluoro(organo)borates and readily available sulfinyl amines are rationally used and converted to a series of alkyl or aryl sulfinamides in moderate to high yields. The reaction allows for the gram-scale preparation of sulfinamides. Moreover, sulfonimidamides, sulfonimidate esters and sulfonyl amides could be obtained in one pot.
引用
收藏
页码:348 / 352
页数:5
相关论文
共 50 条
  • [31] Single-Flask Multicomponent Synthesis of Highly Substituted α-Pyrones via a Sequential Enolate Arylation and Alkenylation Strategy
    Grigalunas, Michael
    Wiest, Olaf
    Helquist, Paul
    ORGANIC LETTERS, 2016, 18 (21) : 5724 - 5727
  • [32] Efficient One-Pot Synthesis of 3-Substituted Phthalides via Additive Arylation of Organozinc Intermediate
    Tonk, Rajiv Kumar
    Yadav, Vivek
    Hasan, Mohsin
    LETTERS IN ORGANIC CHEMISTRY, 2021, 18 (10) : 783 - 789
  • [33] Porous Aromatic Frameworks: Synthesis via Friedel-Crafts Alkylation Reaction and Gas Sorption Property
    Cui Peng
    Jing Xiao-Fei
    Ren Hao
    Yuan Ye
    Zhu Guang-Shan
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2015, 31 (09) : 1855 - 1859
  • [34] Synthesis of Tetramic Acid Derivatives via a Tandem Umpolung Alkylation/Reduction/Cyclization Reaction of γ-Hydrazono β-Ketoester
    Mizota, Isao
    Maeda, Miki
    Imoto, Kiho
    Shimizu, Makoto
    ORGANIC LETTERS, 2020, 22 (08) : 3079 - 3083
  • [35] Synthesis of functionalized primary alkyltrifluoroborates via hydroboration and elimination of auxiliary groups using benzoquinone reductive alkylation
    Zillman, David J.
    Sami, Reman A.
    Daley, Lauren M.
    Polk, Stewart C.
    Hincapie, Gloria C.
    Cole, Thomas E.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2024, 1005
  • [36] Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts
    Schoenbauer, David
    Sambiagio, Carlo
    Noel, Timothy
    Schnuerch, Michael
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 809 - 817
  • [37] Mechanochemical Copper-Catalyzed Synthesis of NH-Sulfonimidamides by Oxidative Amination of Primary Sulfinamides
    Wu, Peng
    Ling, Li
    Hu, Yijie
    Pan, Shulei
    Bolm, Carsten
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2024, 12 (43): : 15875 - 15880
  • [38] Naphthalene Bisimide-Based Acceptor Polymers: Synthesis via Palladium-Catalyzed Direct Arylation, Characterization, and Nanostructure
    Nakabayashi, Kazuhiro
    Yamada, Masaya
    Mori, Hideharu
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (01) : 222 - 226
  • [39] Synthesis of Arylidene-β-lactams via exo-Selective Matsuda-Heck Arylation of Methylene-β-lactams
    Riemer, Nastja
    Riemer, Martin
    Krueger, Mandy
    Clarkson, Guy J.
    Shipman, Michael
    Schmidt, Bernd
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (13): : 8786 - 8796
  • [40] Synthesis of 3-aryl-4-(N-aryl)aminocoumarins via photoredox arylation and the evaluation of their biological activity
    Carneiro, Leonardo S. A.
    Almeida-Souza, Fernando
    Lopes, Yanne S. C.
    Novas, Rachel C., V
    Santos, Kaique B. A.
    Ligiero, Carolina B. P.
    Calabrese, Katia da S.
    Buarque, Camilla D.
    BIOORGANIC CHEMISTRY, 2021, 114