N-Hydroxy sulfonamides as new sulfenylating agents for the functionalization of aromatic compounds

被引:39
|
作者
Wang, Fu-Xiang
Zhou, Shao-Da
Wang, Chengming
Tian, Shi-Kai [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED REGIOSELECTIVE SULFENYLATION; ONE-POT SYNTHESIS; METAL-FREE SULFENYLATION; C-H THIOLATION; SULFONYL HYDRAZIDES; CONTROLLABLE SYNTHESIS; PROPARGYLIC ALCOHOLS; NITRIC-OXIDE; INDOLES; EFFICIENT;
D O I
10.1039/c7ob01390f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented use of N-hydroxy sulfonamides as sulfenylating agents has been established. In the presence of catalytic amounts of iodine and N-hydroxysuccinimide, N-hydroxy sulfonamides participated in sulfenylation with indoles, 7-azaindole, N-methyl pyrrole, and 2-naphthol to afford structurally diverse thioethers in moderate to excellent yields with very high regioselectivity.
引用
收藏
页码:5284 / 5288
页数:5
相关论文
共 50 条
  • [1] DISAPPEARING N-HYDROXY COMPOUNDS
    BECKETT, AH
    NAVAS, GE
    HUTT, AJ
    FARAG, M
    JOURNAL OF PHARMACY AND PHARMACOLOGY, 1979, 31 (07) : 476 - 477
  • [2] GENOTOXICITY OF ALIPHATIC N-HYDROXY COMPOUNDS
    ANDRAE, U
    ZIEGLERSKYLAKAKIS, K
    MUTATION RESEARCH, 1984, 130 (03): : 227 - 227
  • [3] N-HYDROXY COMPOUNDS AS CATALYSTS FOR AMINOLYSIS OF ACTIVATED ESTERS
    KONIG, W
    GEIGER, R
    CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (11): : 3626 - 3635
  • [4] CONJUGATES OF N-HYDROXY METABOLITES OF AROMATIC-AMINES IN DOG URINE
    RADOMSKI, JL
    REY, AA
    BRILL, E
    PROCEEDINGS OF THE AMERICAN ASSOCIATION FOR CANCER RESEARCH, 1973, 14 (MAR): : 126 - &
  • [5] BLADDER CANCER INDUCTION BY AROMATIC AMINES . ROLE OF N-HYDROXY METABOLITES
    RADOMSKI, JL
    BRILL, E
    SCIENCE, 1970, 167 (3920) : 992 - &
  • [6] N-hydroxy sulfonimidamides as new nitroxyl (HNO) donors
    Pennington, RL
    Sha, X
    King, SB
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (09) : 2331 - 2334
  • [7] Metal-free efficient synthesis of aryl sulfonamides from N-hydroxy sulfonamide and amines
    Ramarao, E. V. Venkat Shivaji
    Solanke, Jayshree Nandkumar
    Chatterjee, Rana
    Gat, Savita
    Dhayalan, Vasudevan
    Dandela, Rambabu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (29) : 5918 - 5923
  • [8] N-hydroxy compounds as new internal standards for the 31P-NMR determination of lignin hydroxy functional groups
    Zawadzki, M
    Ragauskas, A
    HOLZFORSCHUNG, 2001, 55 (03) : 283 - 285
  • [9] Metal-Free Direct Oxysulfonylation of Styrenes with N-Hydroxy Aryl Sulfonamides to Access β-Ketosulfones
    Solanke, Jayshree
    Chatterjee, Rana
    Dandela, Rambabu
    CHEMISTRYSELECT, 2024, 9 (48):
  • [10] Redox chemistry in laccase-catalyzed oxidation of N-hydroxy compounds
    Xu, F
    Kulys, JJ
    Duke, K
    Li, KC
    Krikstopaitis, K
    Deussen, HJW
    Abbate, E
    Galinyte, V
    Schneider, P
    APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2000, 66 (05) : 2052 - 2056