Iodine-Promoted Tunable Synthesis of 2-Naphthyl Thioethers and 1-Naphthyl Thioethers

被引：12
作者：
Bao, Yishu [1 ]
Yang, Xiuqin [1 ]
Dai, Zonghao [1 ]
Ji, Suyu [1 ]
Zhou, Qingfa [1 ]
Yang, Fulai [1 ]
机构：
[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 09期
基金：
中国国家自然科学基金;
关键词：
Tetralones; Disulfides; Iodine; Deoxygenation; Synthetic methods; ARYL CHLORIDES; BORONIC ACIDS; SULFIDES; THIOLS; METHYLTHIOLATION; SULFENYLATION; ARYLATION; CARBON;
D O I：
10.1002/adsc.201801562
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An iodine-promoted regioselective sulfenylation/deoxygenation/aromatization reaction of 1-tetralones with disulfides has been developed. This process could be modified to synthesize 2-naphthyl thioethers and 1-naphthyl thioethers in moderate to excellent yields, respectively. Furthermore, when the reaction was extended to 2-tetralones, 2-naphthyl thioethers were obtained as the sole products. The current study bridges the deoxygenation and sulfenylation/aromatization of ketones, thus providing a new tool in organic synthesis.
引用
收藏
页码：2154 / 2158
页数：5
相关论文
共 48 条
  • [1] RECENT APPLICATIONS OF THE SHAPIRO REACTION
    ADLINGTON, RM
    BARRETT, AGM
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) : 55 - 59
  • [2] Microwave assisted synthesis of 1-(arylthio)naphthalen-2-ols and their antimicrobial activity
    Anjaiah, Ch.
    Nagamani, M.
    Lincoln, Ch. Abraham
    Ashok, D.
    [J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (12) : 2930 - 2932
  • [3] Rhodium-catalyzed α-methylthiolation reaction of unactivated ketones using 1,2-diphenyl-2-methylthio-1-ethanone for the methylthio transfer reagent
    Arisawa, Mieko
    Toriyama, Fumihiko
    Yamaguchi, Masahiko
    [J]. TETRAHEDRON, 2011, 67 (12) : 2305 - 2312
  • [4] BAMFORD WR, J CHEM SOC
  • [5] Iodine-Promoted Deoxygenative Iodization/Olefination/Sulfenylation of Ketones with Sulfonyl Hydrazides: Access to β-lodoalkenyl Sulfides
    Bao, Yishu
    Yang, Xiuqin
    Zhou, Qingfa
    Yang, Fulai
    [J]. ORGANIC LETTERS, 2018, 20 (07) : 1966 - 1969
  • [6] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [7] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
    Beletskaya, Irina P.
    Ananikov, Valentine P.
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
  • [8] Bernardi F., 1985, THEORETICAL EXPT ADV, V19
  • [9] CLEMMENSEN REDUCTION OF DIFUNCTIONAL KETONES
    BUCHANAN, JG
    WOODGATE, PD
    [J]. QUARTERLY REVIEWS, 1969, 23 (04): : 522 - &
  • [10] Chamberlin A.R., 1990, Org. React, V39, P1
12345