Palladium-Catalyzed Thiocarbonylation of Aryl Iodides with S-Aryl Thioformates via Thioester Transfer

被引:12
|
作者
Yang, Ruiting [1 ]
Xie, Qiumin [1 ]
Yan, Qian [1 ]
Zhang, Xiuli [1 ]
Gao, Bao [1 ]
机构
[1] Anhui Agr Univ, Sch Sci, Hefei 230036, Peoples R China
基金
中国国家自然科学基金;
关键词
THIOLS; CARBONYLATION; THIOETHERS; HALIDES; VINYL;
D O I
10.1021/acs.orglett.2c02953
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we reported a novel approach to synthesize thioesters with S-aryl thioformates as thioester sources. The reaction proceeded at ambient temperature using widely available starting ingredients, wherein the thioester moiety was smoothly transferred to aryl iodides from S-aryl thioformates. A variety of substrates with various electronic natures were all tolerated under the reaction conditions to furnish desirable thioesters in ranges from moderate to excellent yields. The gram-scale reaction was also conducted, and there was virtually little change in chemical yield, indicating that large-scale synthesis of thioesters may be viable using this method.
引用
收藏
页码:7555 / 7559
页数:5
相关论文
共 50 条
  • [1] Palladium-Catalyzed Cyclization/Thiocarbonylation for the Synthesis of Thioester-Substituted Benzofurans with S-Aryl Thioformates as the Thioester Sources
    Ge, Xing
    Lin, De-Jiang
    Qi, Xinxin
    Wu, Xiao-Feng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (48)
  • [2] Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides
    Kim, Yeojin
    Song, Kwang Ho
    Lee, Sunwoo
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (19): : 2938 - 2943
  • [3] Palladium-Catalyzed Thiocarbonylative Synthesis of α,β-Unsaturated Thioesters Using S-Aryl Thioformates as the Thioester Sources
    Shen, Zekai
    Huo, Yong-Wang
    Qi, Xinxin
    Wu, Xiao-Feng
    ORGANIC LETTERS, 2023, 25 (22) : 4140 - 4144
  • [4] Palladium-catalyzed carbonylation of thioacetates and aryl iodides for the synthesis of S-aryl thioesters
    Kim, Myungjin
    Yu, Subeen
    Kim, Jeung Gon
    Lee, Sunwoo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (16): : 2447 - 2452
  • [5] Palladium-Catalyzed Thiocarbonylation of Aryl Iodides Using CO2
    Wang, Huan
    Li, Yudong
    Sun, Yajun
    Li, Yuehui
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 8835 - 8842
  • [6] Palladium-catalyzed amination of aryl iodides
    Wolfe, JP
    Buchwald, SL
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03): : 1133 - 1135
  • [7] Palladium-Catalyzed Thiocarbonylation of Aryl, Vinyl, and Benzyl Bromides
    Burhardt, Mia N.
    Ahlburg, Andreas
    Skrydstrup, Troels
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (24): : 11830 - 11840
  • [8] STYRENE DERIVATIVES VIA PALLADIUM-CATALYZED VINYLATION OF ARYL IODIDES
    HALLBERG, A
    WESTERLUND, C
    CHEMISTRY LETTERS, 1982, (12) : 1993 - 1994
  • [9] Palladium-Catalyzed Carbonylation of Aryl Iodides with Sulfinamides
    Belfrage, Anna Karin
    Wakchaure, Prasad
    Larhed, Mats
    Sandstrom, Anja
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (32) : 7069 - 7074
  • [10] PALLADIUM-CATALYZED ANNELATION OF ARYL IODIDES WITH DIPHENYLACETYLENE
    WU, G
    RHEINGOLD, AL
    GEIB, SJ
    HECK, RF
    ORGANOMETALLICS, 1987, 6 (09) : 1941 - 1946