Transition-Metal-Free C-H Trifluoromethylthiolation of N,N-Disubstituted Enaminones To Access CF3S-Functionalized Enaminones and Their Application in the Synthesis of CF3S-Heteroaryls

被引：6

作者：

Ying, Jinbiao ^{[1
]}

Zhou, Tao ^{[1
]}

Liu, Yunyun ^{[1
]}

Zhou, Liyun ^{[1
]}

Wan, Jie-Ping ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330033, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 12期

基金：

中国国家自然科学基金;

关键词：

BOND FORMATION; FUNCTIONALIZATION; ACYLOXYLATION; AMINES;

D O I：

10.1021/acs.joc.4c00704

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alpha-C-H trifluoromethylthiolation of N,N-disubstituted enaminones has been achieved with simple and cheap CF3SO2Na as the CF3S source. The reactions were run at mild temperature (0 degrees C to rt) using POCl3 as the only reducing reagent. The work represents the first example on the synthesis of alpha-trifluoromethylthio enaminones via direct C-H functionalization. In addition, the resulting CF3S-functionalized enaminones have been proven as useful building blocks in the synthesis of various CF3S-functionalized heteroaromatic compounds by simple annulation reactions.

引用

页码：9078 / 9085

页数：8

共 50 条

[31] Transition-Metal-Free C(sp3)-S Coupling in Water: Synthesis of Benzyl Dithiocarbamates Using Thiuram Disulfides as an Organosulfur Source
Peng, Han-Ying
Dong, Zhi-Bing
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (05) : 949 - 956
[32] [METHYLENEBIS(N,N'-DIMETHYLUREA)]HYDROGEN(I) TRIFLUOROMETHANESULFONATE, C7H17N4O2+.CF3O3S- - A VERY STRONG INTRAMOLECULAR O...H...O BOND
MAAS, G
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1985, 41 (JUL) : 1133 - 1136
[33] Transition-Metal-Free Selective Oxidative C(sp3)-S/Se Coupling of Oxindoles, Tetralone, and Arylacetamides: Synthesis of Unsymmetrical Organochalcogenides
Prasad, Ch. Durga
Sattar, Moh
Kumar, Sangit
ORGANIC LETTERS, 2017, 19 (04) : 774 - 777
[34] Transition-metal-free Chemoselective Oxidative C-C Coupling of the sp3 C-H Bond of Oxindoles with Arenes and Addition to Alkene: Synthesis of 3-Aryl Oxindoles, and Benzofuro- and Indoloindoles
Sattar, Moh.
Rathore, Vandana
Prasad, Ch. Durga
Kumar, Sangit
CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (07) : 734 - 743
[35] Palladium and Copper Cocatalyzed Tandem N-H/C-H Bond Functionalization: Synthesis of CF3-Containing Indolo- and Pyrrolo[2,1-a]isoquinolines
Sun, Lei-Lei
Liao, Zhi-Yong
Tang, Ri-Yuan
Deng, Chen-Liang
Zhang, Xing-Guo
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06): : 2850 - 2856
[36] Synthesis of CF3-Substituted N-Heterocyclic Compounds Based on C-H Activation-Initiated Formal [2+3] Annulation Featuring with a Latent Nucleophilic Site
Wang, Manqing
Yan, Shengnan
Li, Bin
Hou, Huihang
Ma, Chunhua
Zhang, Xinying
Fan, Xuesen
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7828 - 7842
[37] Oxidative C(Sp3)-H activation and C-N cleavage of N-methyl amines under transition-metal-free condition for synthesis of methylene-bridged bis-1,3-diketones
Wang, Xiaohu
Wang, Yi
Yuan, Yu
Xing, Chun-Hui
TETRAHEDRON, 2014, 70 (12) : 2195 - 2202
[38] Transition-Metal-Free Dehydrogenation of Benzyl Alcohol for C-C and C-N Bond Formation for the Synthesis of Pyrazolo[3,4-b]pyridine and Pyrazoline Derivatives
Annes, Sesuraj Babiola
Perumal, Karuppaiah
Anandhakumar, Kalaiselvan
Shankar, Bhaskaran
Ramesh, Subburethinam
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09): : 6039 - 6057
[39] COPPER(I) COMPLEXES OF 14-MEMBERED AND 16-MEMBERED CHELATING MACROCYCLES WITH TRANS-DISPOSED PAIRS OF IMINE-N AND THIOETHER-S DONORS - CRYSTAL AND MOLECULAR-STRUCTURES OF [CU(C18H18N2S2)]CF3SO3 AND [CU(C20H22N2S2)]CF3SO3
MARTIN, JWL
ORGAN, GJ
WAINWRIGHT, KP
WEERASURIA, KDV
WILLIS, AC
WILD, SB
INORGANIC CHEMISTRY, 1987, 26 (18) : 2963 - 2968
[40] Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones, and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of sp3 and sp2 C-H Bonds
Rathore, Vandana
Sattar, Moh.
Kumar, Raushan
Kumar, Sangit
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9206 - 9218

← 1 2 3 4 5 →