Pd-Catalyzed Diastereoselective Trifluoromethylthiolation of Functionalized Acrylamides

被引：42

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

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 19期

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

页码：5106 / 5109

页数：4

共 50 条

[1] Pd-Catalyzed Trifluoromethylthiolation of Unsaturated Compounds: A General Approach
Zhao, Qun
Chen, Mu-Yi
Poisson, Thomas
Pannecoucke, Xavier
Bouillon, Jean-Philippe
Besset, Tatiana
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (44) : 6167 - 6175
[2] Pd-Catalyzed Selective Chlorination of Acrylamides at Room Temperature
Chen, Mu-Yi
Pannecoucke, Xavier
Jubault, Philippe
Besset, Tatiana
ORGANIC LETTERS, 2020, 22 (19) : 7556 - 7561
[3] Pd-Catalyzed Enantioselective Hydroamidocarbonylation of α-Substituted Acrylamides to Chiral Succinimides
Shi, Zhanglin
Ji, Xiaolei
Shen, Chaoren
Dong, Kaiwu
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (08): : 5036 - 5043
[4] A Pd-Catalyzed Synthesis of Functionalized Piperidines
Allen, Benjamin D. W.
Connolly, Matthew J.
Harrity, Joseph P. A.
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (37) : 12999 - 13003
[5] Pd-catalyzed synthesis of highly functionalized piperidines
Allen, Benjamin
Harrity, Joseph
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[6] Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement
Li, Jiagen
Wang, Ming
Jiang, Xuefeng
ORGANIC LETTERS, 2021, 23 (23) : 9053 - 9057
[7] Pd-Catalyzed Dehydrogenative Oxidation of Alcohols to Functionalized Molecules
Mori, Takamichi
Ishii, Chihiro
Kimura, Masanari
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (08) : 1709 - 1717
[8] Diastereoselective Pd-Catalyzed Domino Heck/Arylborylation Sequence Forming Borylated Chromans
Yoon, Hyung
Jang, Young Jin
Lautens, Mark
SYNTHESIS-STUTTGART, 2016, 48 (10): : 1483 - 1490
[9] Access to Isothiazolones from Simple Acrylamides by Pd-Catalyzed C-H Bond Activation
Chen, Mu-Yi
Pannecoucke, Xavier
Jubault, Philippe
Besset, Tatiana
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 13194 - 13202
[10] Ni- and Pd-Catalyzed Synthesis of Substituted and Functionalized Allylic Boronates
Zhang, Ping
Roundtree, Ian A.
Morken, James P.
ORGANIC LETTERS, 2012, 14 (06) : 1416 - 1419

← 1 2 3 4 5 →