I2/TBHP-mediated reaction of sulfonylhydrazides with alkynes: synthesis of (E)-β-iodovinyl sulfones

被引:81
|
作者
Li, Xiaoqing [1 ]
Xu, Xiangsheng [1 ]
Shi, Xinhua [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China
基金
美国国家科学基金会;
关键词
(E)-beta-iodovinyl sulfones; Sulfonylhydrazides; TBHP; Sulfonyl radicals; Atom economy; CATALYZED ALLYLIC SULFONYLATION; METAL-FREE; VINYL SULFONES; 1,3-DIPOLAR CYCLOADDITION; OXIDATIVE AMINATION; AZOMETHINE YLIDES; BONDS; ALKENES; TBHP;
D O I
10.1016/j.tetlet.2013.03.117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and simple procedure for the syntheses of (E)-beta-iodovinyl sulfones through TBHP mediated reaction of sulfonylhydrazides and iodine with aryl acetylenes has been developed. This method offers several advantages such as high atom economy, environmentally benign oxidant, less byproduct, and easy operation. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3071 / 3074
页数:4
相关论文
共 50 条
  • [41] Synthesis of Amides from Aliphatic Acids and Amines by using of I2/TBHP at Room Temperature
    Sirgamalla, Rambabu
    Kommakula, Ashok
    Banoth, Sonyanaik
    Dharavath, Ravi
    Adem, Kurumanna
    Madhu, P.
    Boda, Sakram
    CHEMISTRYSELECT, 2018, 3 (04): : 1062 - 1065
  • [42] Metal-free synthesis of 2-aminothiadiazoles via TBHP-Mediated oxidative C-S bond formation
    Hatvate, Navnath T.
    Ghodse, Shrikant M.
    Telvekar, Vikas N.
    SYNTHETIC COMMUNICATIONS, 2018, 48 (03) : 285 - 290
  • [43] Base-mediated [3+2]-cycloannulation strategy for the synthesis of pyrazolo[1,5-a]pyridine derivatives using (E)-β-iodovinyl sulfones
    Jannapu Reddy, Raju
    Sharadha, Nunavath
    Haritha Kumari, Arram
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (21) : 4331 - 4337
  • [44] AN IMPROVED SYNTHESIS OF VINYL- AND β-IODOVINYL SULFONES BY A MOLECULAR IODINE-MEDIATED ONE-POT IODOSULFONATION-DEHYDROIODINATION REACTION
    Sawangphon, Tassaporn
    Katrun, Praewpan
    Chaisiwamongkhol, Korbua
    Pohmakotr, Manat
    Reutrakul, Vichai
    Jaipetch, Thaworn
    Soorukram, Darunee
    Kuhakarn, Chutima
    SYNTHETIC COMMUNICATIONS, 2013, 43 (12) : 1692 - 1707
  • [45] IBX/I2-Mediated Reaction of Sodium Arenesulfinates with Alkenes: Facile Synthesis of β-Keto Sulfones
    Samakkanad, Natthapol
    Katrun, Praewpan
    Techajaroonjit, Thanachart
    Hlekhlai, Sornsiri
    Pohmakotr, Manat
    Reutrakul, Vichai
    Jaipetch, Thaworn
    Soorukram, Darunee
    Kuhakarn, Chutima
    SYNTHESIS-STUTTGART, 2012, 44 (11): : 1693 - 1699
  • [46] I2/TBHP Mediated C-N and C-H Bond Cleavage of Tertiary Amines toward Selective Synthesis of Sulfonamides and β-Arylsulfonyl Enamines: The Solvent Effect on Reaction
    Lai, Junyi
    Chang, Liming
    Yuan, Gaoqing
    ORGANIC LETTERS, 2016, 18 (13) : 3194 - 3197
  • [47] Synthesis of Sulfonated 5-Aminopyrazoles by I2/Benzoyl Peroxide-Mediated Tandem Reaction
    Cheng, Dongping
    Chen, Tianpeng
    Xu, Xiaoliang
    Yan, Jizhong
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (05) : 901 - 904
  • [48] Greening the Synthesis of 2,3-Dihydrobenzofuran Selenides: I2/TBHP-Promoted Selenocyclization of 2-Allylphenols
    Bartz, Ricardo H.
    Souza, Pedro S.
    Iarocz, Lucas E. B.
    Hellwig, Paola S.
    Jacob, Raquel G.
    Silva, Marcio S.
    Lenardao, Eder J.
    Perin, Gelson
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (07)
  • [49] Intramolecular oxidative rearrangement: I2/TBHP/DMSO-mediated metal free facile access to quinoxalinone derivatives
    Slathia, Nancy
    Gupta, Annah
    Kapoor, Kamal K.
    TETRAHEDRON LETTERS, 2021, 78
  • [50] I2/TBHP Mediated Divergent C(sp2)-P Cleavage of Allenylphosphine Oxides: Substituent-Controlled Regioselectivity
    Liu, Teng
    Zhu, Jie
    Sun, Xue
    Cheng, Liang
    Wu, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (15) : 3532 - 3537