Pd-Catalyzed Diastereoselective Trifluoromethylthiolation of Functionalized Acrylamides

被引:43
作者
Zhao, Qun [1 ]
Poisson, Thomas [1 ]
Pannecoucke, Xavier [1 ]
Bouillon, Jean -Philippe [1 ]
Besset, Tatiana [1 ]
机构
[1] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA UMR 6014, F-76000 Rouen, France
关键词
COPPER-MEDIATED TRIFLUOROMETHYLTHIOLATION; HYPERVALENT IODONIUM YLIDE; BORONIC ACIDS; ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION; SILVER(I) TRIFLUOROMETHANETHIOLATE; SUBSTITUENT CONSTANTS; RECENT PROGRESS; FLUORINE; ALKENES; ARYL;
D O I
10.1021/acs.orglett.7b02384
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Pd-catalyzed diastereos elective trifluoromethylthiolation of acrylamides was developed to allow the formation of the Z-isomer as a single product. Using a C-H bond functionalization strategy, the method was applied to a broad range of a aryl, alpha-alkyl, and alpha,beta-disubstituted acrylamides bearing the amide derived from the 8-aminoquinoline as a directing group. Mechanistic studies as well as postfunctionalization of the products were performed. This approach opens new routes to unprecedented SCF3-containing scaffolds.
引用
收藏
页码:5106 / 5109
页数:4
相关论文
共 50 条
  • [21] Pd-Catalyzed Olefination of Perfluoroarenes with Allyl Esters
    Li, Zejiang
    Zhang, Yuexia
    Liu, Zhong-Quan
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 74 - 77
  • [22] Pd-Catalyzed Regioselective Hydrocarboxylation of Alkyl Terminal Olefins with Oxalic Acid
    Ren, Wenlong
    Sheng, Xujian
    Shi, Yian
    [J]. ORGANIC LETTERS, 2024, 26 (29) : 6174 - 6178
  • [23] Pd-Catalyzed Synthesis of γ-Keto Esters as Key Intermediates for the Synthesis of γ-Hydroxybutenolides
    Schacht, Mathias
    Mohammadi, Djawid
    Schuetzenmeister, Nina
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (15) : 2587 - 2591
  • [24] Aromatic Trifluoromethylselenolation via Pd-catalyzed C-H functionalization
    Grollier, Kevin
    Chefdeville, Emmanuel
    Jeanneau, Erwann
    Billard, Thierry
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (50) : 12910 - 12916
  • [25] Diastereoselective Pd-Catalyzed Anomeric C(sp3)-H Activation: Synthesis of α-(Hetero)aryl C-Glycosides
    Ghouilem, Juba
    Tran, Christine
    Grimblat, Nicolas
    Retailleau, Pascal
    Alami, Mouad
    Gandon, Vincent
    Messaoudi, Samir
    [J]. ACS CATALYSIS, 2021, 11 (03) : 1818 - 1826
  • [26] Pd-catalyzed synthesis of functionalized arylketones from boronic acids and carboxylic acids activated in situ with dimethyl dicarbonate
    Goossen, LJ
    Winkel, L
    Döhring, A
    Ghosh, K
    Paetzold, J
    [J]. SYNLETT, 2002, (08) : 1237 - 1240
  • [27] A facile approach to synthesize azaindoline functionalized spirocarbocyclic scaffolds via a Pd-catalyzed cascade cyclization/dearomatization process
    Wu, Xin-Xing
    Tian, Hui
    Wang, Yu
    Liu, Anjia
    Chen, Hengfan
    Fan, Zhixiang
    Li, Xuefeng
    Chen, Shufeng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (22): : 3310 - 3314
  • [28] Pd-Catalyzed Arylperfluoroalkylation of Unactivated Olefins for the Synthesis of Heterocycles
    Zheng, Jinhua
    Chen, Pan
    Yuan, Yaofeng
    Cheng, Jiajia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11) : 5790 - 5797
  • [29] An effective Pd-catalyzed hydroxycarbonylation of olefins with CO and HCOOH
    Eliseev, Oleg L.
    Bondarenko, Tatyana N.
    Tsapkina, Maria V.
    [J]. MENDELEEV COMMUNICATIONS, 2022, 32 (02) : 253 - 255
  • [30] Highly Selective Pd-Catalyzed Intermolecular Fluorosulfonylation of Styrenes
    Yuan, Zheliang
    Wang, Hao-Yang
    Mu, Xin
    Chen, Pinhong
    Guo, Yin-Long
    Liu, Guosheng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) : 2468 - 2471