Synthesis of α-sulfonyloxyketones via iodobenzene diacetate (PIDA)-mediated oxysulfonyloxylation of alkynes with sulfonic acids

被引:5
|
作者
Zhang, Yang [1 ]
Tan, Hua [1 ]
Liu, Weibing [1 ]
机构
[1] Guangdong Univ Petrochem Technol, Coll Chem Engn, 2 Guandu Rd, Maoming 525000, Peoples R China
来源
RSC ADVANCES | 2017年 / 7卷 / 85期
关键词
HYPERVALENT IODINE REAGENT; TOSYLOXY KETONES; PHASE;
D O I
10.1039/c7ra11875a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple yet powerful method to synthesize a variety of a-sulfonyloxyketones has been developed. This novel method can be applied for the direct oxysulfonyloxylation of alkynes with sulfonic acids to access a variety of alpha-sulfonyloxyketones. Compared to the reported methods for the application of PIDA, this study expands its application scope and uses it not only as the oxidant but also as the carrier of "O" to form the carbonyl group in the products. In addition, under the established conditions, this methodology not only exhibits a broad substrate scope but also demonstrates exclusive regioselectivity with substrates of 1,2-disubstituted internal alkynes.
引用
收藏
页码:54017 / 54020
页数:4
相关论文
共 50 条
  • [41] Synthesis of Spiro[benzofuran-2,2'-benzo[b]thiophene]-3,3'-diones via PIDA/CuBr-Mediated Spirocyclization
    Li, Xuemin
    Liang, Huiyuan
    Yang, Yaxin O.
    Wang, Xi
    Zhang, Jingran
    Wang, Donghua
    Sun, Fengxia
    Du, Yunfei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (42) : 6563 - 6569
  • [42] A convenient synthesis of indoloquinolinones via 3-arylation of indole-2-carboxamides and PIDA-mediated C-N bond formation
    Li, Yulin
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    TETRAHEDRON, 2015, 71 (19) : 2927 - 2935
  • [43] Photosensitizer-free synthesis of β-keto sulfones via visible-light-induced oxysulfonylation of alkenes with sulfonic acids
    Peng, Zhen
    Hong, Yun-Yun
    Peng, Sha
    Xu, Xiang-Qun
    Tang, Shan-Shan
    Yang, Li-Hua
    Xie, Long-Yong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (20) : 4537 - 4541
  • [44] Synthesis of isocoumarins via Pd/C-mediated reactions of o-iodobenzoic acid with terminal alkynes
    Subramanian, V
    Batchu, VR
    Barange, D
    Pal, M
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12): : 4778 - 4783
  • [46] Stereoselective synthesis of fluoroalkylated (Z)-alkene via nickel-catalyzed and iron-mediated hydrofluoroalkylation of alkynes
    Li, Xiang-Rui
    Li, Wen-Xin
    Zhang, Zhuo-Wen
    Shen, Chuanji
    Zhou, Xiaocong
    Chu, Xue-Qiang
    Rao, Weidong
    Shen, Zhi-Liang
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (22) : 6377 - 6383
  • [47] Synthesis of polysubstituted pyrroles via Ag(I)-mediated conjugate addition and cyclization reaction of terminal alkynes with amines
    Chong, Qinglei
    Xin, Xiaoyi
    Wang, Chunxiang
    Wu, Fan
    Wan, Boshun
    TETRAHEDRON, 2014, 70 (02) : 490 - 494
  • [48] Synthesis of acyloxy-2H-azirine and sulfonyloxy-2H-azirine derivatives via a one-pot reaction of β-enamino esters, PIDA and carboxylic acid or sulfonic acid
    Tang, Pan
    Wen, Long
    Ma, Hao-Jie
    Yang, Yi
    Jiang, Yan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (15) : 3061 - 3066
  • [49] Synthesis of phosphaisocoumarin acids via Me3SiX-mediated dealkylation reaction
    Peng, Ai-Yun
    Li, Baojian
    Yang, Xun
    Lin, Junying
    SYNTHESIS-STUTTGART, 2008, (15): : 2412 - 2416
  • [50] Synthesis of allylic sulfonic acids via regioselective Pd-catalyzed allylic substitutions of Na2SO3
    Liu, Wei
    Zhao, Xiaoming
    TETRAHEDRON LETTERS, 2015, 56 (48) : 6800 - 6802