Visible-Light-Mediated Synthesis of α-Halomethyl Ketones from Terminal Alkynes

被引:2
作者
Shah, Iftkhar Hussain [1 ,3 ]
Kumar, Sourav [1 ,3 ]
Kumar, Jaswant [1 ,3 ]
Raheem, Shabnam [2 ]
Rizvi, Masood Ahmad [2 ]
Shah, Bhahwal Ali [1 ,3 ]
机构
[1] Acad Sci & Ind Res AcSIR, Ghaziabad 201002, India
[2] Univ Kashmir, Srinagar 190006, India
[3] CSIR Indian Inst Integrat Med, Nat Prod & Med Chem, Canal Rd, Jammu 180001, India
关键词
alpha-halomethyl ketones; alkynes; N-halosuccinimide; radicals; trifluoroacetic acid; CATALYZED HYDRATION; N-HALOSUCCINIMIDES; CASCADE REACTION; MILD; HALOGENATION; FUNCTIONALIZATION; HALOKETONES; DERIVATIVES; HALOALKYNES; CONVENIENT;
D O I
10.1002/cptc.202100231
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
A visible-light-assisted approach for the synthesis of alpha-halomethyl ketones from terminal alkynes has been developed. The reaction introduces halogen at the alpha-position of terminal alkynes using N-halosuccinimides as the halogen source. It relies on the photodegradation of N-halosuccinimides obviating the requirement for a photocatalyst. The procedure enables the synthesis of a diverse range of alpha-haloketones from different aromatic bromo- and iodoalkynes.
引用
收藏
页数:5
相关论文
共 55 条
  • [31] SYNTHETIC METHODS AND REACTIONS .123. PREPARATION OF ALPHA-CHLORO KETONES FROM ENOL SILYL ETHERS WITH SULFURYL CHLORIDE FLUORIDE AND SULFURYL CHLORIDE
    OLAH, GA
    OHANNESIAN, L
    ARVANAGHI, M
    PRAKASH, GKS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) : 2032 - 2034
  • [32] Synthesis and anti-VZV activity of 6-heteroaryl derivatives of tricyclic acyclovir and 9-{[cis-1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl}guanine analogues
    Ostrowski, Tomasz
    Golankiewicz, Bozenna
    De Clercq, Erik
    Andrei, Graciela
    Snoeck, Robert
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (08) : 3313 - 3317
  • [33] α-Amino-α′-Halomethylketones: Synthetic Methodologies and Pharmaceutical Applications as Serine and Cysteine Protease Inhibitors
    Pace, Vittorio
    Castoldi, Laura
    Pregnolato, Massimo
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2013, 13 (07) : 988 - 996
  • [34] Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
    Patil, Rajendra D.
    Joshi, Girdhar
    Adimurthy, Subbarayappa
    Ranu, Brindaban C.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (21) : 2529 - 2532
  • [35] Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions
    Pravst, Igor
    Zupan, Marko
    Stavber, Stojan
    [J]. TETRAHEDRON, 2008, 64 (22) : 5191 - 5199
  • [36] TsNBr2 mediated oxidative functionalization of alkynes
    Rajbongshi, Kamal Krishna
    Hazarika, Debojit
    Phukan, Prodeep
    [J]. TETRAHEDRON, 2016, 72 (29) : 4151 - 4158
  • [37] Synthesis of α-Functionalized Trichloromethylcarbinols
    Ram, Ram N.
    Soni, Vineet Kumar
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17) : 8922 - 8928
  • [38] A mild preparation of α-halo-α,β-enones from cyclic enones.
    Righi, G
    Bovicelli, P
    Sperandio, A
    [J]. TETRAHEDRON LETTERS, 1999, 40 (32) : 5889 - 5892
  • [39] C-H functionalization reactions enabled by hydrogen atom transfer to carbon-centered radicals
    Sarkar, Sumon
    Cheung, Kelvin Pak Shing
    Gevorgyan, Vladimir
    [J]. CHEMICAL SCIENCE, 2020, 11 (48) : 12974 - 12993
  • [40] Aerobic oxysulfonylation of alkenes using thiophenols: an efficient one-pot route to β-ketosulfones
    Singh, Atul K.
    Chawla, Ruchi
    Keshari, Twinkle
    Yadav, Vinod K.
    Yadav, Lal Dhar S.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (42) : 8550 - 8554