Electrochemical Oxidative Arylsulfonylation and 1,2-Alkyl Shift Sequences of Alkenyl Cyclobutanols for the Synthesis of β-Sulfonated Cyclopentanones

被引：17
|
作者：
Kim, Yebin [1 ,2 ]
Kim, Dae Young [1 ,2 ]
机构：
[1] Soonchunhyang Univ, Dept Chem, Asan 31538, Chungnam, South Korea
[2] Soonchunhyang Univ, Dept ICT Environm Hlth Syst, Asan 31538, Chungnam, South Korea
来源：
BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2021年 / 42卷 / 03期
基金：
新加坡国家研究基金会;
关键词：
Electrochemical oxidation; Sulfonylation; Vinyl cyclobutanols; beta-Sulfonated cyclopentanones; Semipinacol rearrangement; VISIBLE-LIGHT PHOTOREDOX; MIGRATION SEQUENCES; RING EXPANSION; SEMIPINACOL REARRANGEMENTS; ELECTROCATALYTIC APPROACH; DIFUNCTIONALIZATION; QUINOXALIN-2(1H)-ONES; SULFONYLATION; CYCLIZATION; ARYLATION;
D O I：
10.1002/bkcs.12218
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel process for the synthesis of beta-sulfonated cyclopentanones via electrochemical oxidative radical arylsulfonylation and 1,2-alkyl shift sequences of vinyl cyclobutanols was successfully developed. This approach represents a practical method for the preparation of beta-sulfonated cyclopentanones under environmentally benign reaction conditions.
引用
收藏
页码：510 / 513
页数：4
相关论文
共 38 条
  • [31] Synthesis and oxidative cleavage of 1-and 2-alkyl derivatives of (exo,exo)5,6-dihydroxy-4,5,6,7-tetrahydro-4,7,-methanoindazoles
    García, MD
    Caamaño, O
    Fernández, F
    Figueira, MJ
    Gómez, G
    [J]. SYNTHESIS-STUTTGART, 2003, (14): : 2138 - 2144
  • [32] THE DIRECT ELECTROCHEMICAL SYNTHESIS OF TIN(II) DERIVATIVES OF AROMATIC 1,2-DIOLS, AND A STUDY OF THEIR OXIDATIVE ADDITION-REACTIONS
    MABROUK, HE
    TUCK, DG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1988, (10): : 2539 - 2543
  • [33] Efficient synthesis of 2-deoxy L-ribose from L-arabinose: Mechanistic information on the 1,2-acyloxy shift in alkyl radicals
    Jung, ME
    Xu, Y
    [J]. ORGANIC LETTERS, 1999, 1 (10) : 1517 - 1519
  • [34] Preparation of cis-5-methoxy-and-7-methoxy-1-acetoxy-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone. An epoxide-arene reaction involving a selective 1,2-alkyl shift rearrangement.
    Garg, N
    Gogoll, A
    Westerlund, C
    Sundell, S
    Karlen, A
    Hallberg, A
    [J]. TETRAHEDRON, 1996, 52 (48) : 15209 - 15224
  • [35] Divergence in the Reactivity between Amine- and Phosphine-Catalyzed Cycloaddition Reactions of Allenoates with Enynals: One-Pot Gold-Catalyzed Synthesis of Trisubstituted Benzofurans from the [3+2] Cycloadduct via 1,2-Alkyl Migration and Dehydrogenation
    Kumari, A. Leela Siva
    Swamy, K. C. Kumara
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08): : 4084 - 4096
  • [36] THIOUREA DERIVATIVES OF CARBOHYDRATES .6. SYNTHESIS OF 1,3,4,6-TETRA-O-ACETYL-2-[3-ALKYL(ARYL)-THIOUREIDO]-2-DEOXY-ALPHA-D-GLUCOPYRANOSES AND THEIR TRANSFORMATION INTO 2-ALKYL(ARYL)AMINO-(1,2-DIDEOXY-ALPHA-D-GLUCOPYRANO)[2,1-D]-2-THIAZOLINES
    GONZALEZ, MA
    MOTA, JF
    MONTERREY, IMG
    REQUEJO, JLJ
    ALBARRAN, JCP
    MELLET, MCO
    [J]. CARBOHYDRATE RESEARCH, 1986, 154 : 49 - 62
  • [37] Electrochemical Synthesis of 2-Aryl-3-(2-aminoaryl)quinoxalines via Oxidative Dearomatization/Ring-Opening/Cyclization Cascade Sequence of 2-Arylindoles with 1,2-Diaminoarenes
    Nagare, Yadav Kacharu
    Yadav, Jyothi
    Dolas, Atul Jankiram
    Shah, Imtiyaz Ahmad
    Rangan, Krishnan
    Choudhary, Rahul
    Iype, Eldhose
    Kumar, Indresh
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 11111 - 11121
  • [38] Efficient two-step synthesis of 3-halo-3-enals or 2-halo-2-alkenyl ketones from propargylic bromides via a unique cationic 1,2-aryl or proton shift in electrophilic addition reaction of 2,3-allenols with X+
    Fu, CL
    Li, J
    Ma, SM
    [J]. CHEMICAL COMMUNICATIONS, 2005, (32) : 4119 - 4121
1234