Palladium-Catalyzed Desulfurative Amide Formation from Thioureas and Arylboronic Acids
The development of the reactivity on carbene complexes would lead to the creation of novel synthetic strategies. We discovered herein the Pd-catalyzed desulfurative amide formation involved Suzuki-Miyaura coupling reaction, notably the Pd complex was generated in situ from thioureas, Ag salt and Pd catalyst. Silver salt was essential for the construction of this type of carbenes from available and stable thioureas and well participated in the catalytic cycle. We report a method for the synthesis of arylamides from arylboronic acids, which greatly enriched the application of thiourea chemistry and expanded the application of the Suzuki-Miyaura coupling.
Su, Jianke,Li, Wendong,Li, Xin,Xu, Jian,Song, Qiuling
p. 5664 - 5668
(2020/10/02)
Copper-Catalyzed Carbonylative Cross-Coupling of Arylboronic Acids with N-Chloroamines for the Synthesis of Aryl Amides
A novel copper-catalyzed carbonylative cross-coupling between N-chloroamines and arylboronics acids has been developed. With copper(I) oxide as the catalyst, various desired amide compounds were produced in moderate to good yields. Functional groups such as iodide and alkene are tolerated. Notably, this is the first example of a copper-catalyzed aminocarbonylation with N-chloroamines.
Palladium-catalyzed aminocarbonylation of N-chloroamines with boronic acids
Abstract Aryl (pseudo)halide-based (C-X) carbonylation reactions have been extensively studied during the past few decades. From both academic and synthetic points of view, the carbonylative transformation of N-X bonds represents an interesting and attractive area of investigation. In light of this, the first carbonylative cross-coupling between N-chloroamines and organoboronic acids has been developed. This new type of aminocarbonylation proceeds at mild temperatures (45-55 °C) with 2 mol % Pd/C (10 wt %) as the ligand-free catalyst. Not only arylboronic acids, but also alkenyl- and alkylboronic acids can be applied as the substrates and bromide and iodide substituents in the substrates are well tolerated. Initial mechanistic investigations have also been performed. Umpolung aminocarbonylation: The first palladium-catalyzed carbonylative cross-coupling between N-chloroamines and organoboronic acids has been realized. Various amides were isolated in moderate to excellent yields from reactions under mild temperatures with ligand-free Pd/C as the catalyst. Not only arylboronic acids, but also alkenyl- and alkylboronic acids are applied as the substrates and bromide and iodide substituents in the substrates are well tolerated.
Li, Wanfang,Wu, Xiao-Feng
supporting information
p. 7374 - 7378
(2015/05/27)
Ruthenium-catalyzed ortho-C-H halogenations of benzamides
[Ru3(CO)12] and AgO2C(1-Ad) enabled the first ruthenium-catalyzed intermolecular halogenations of arenes via C-H activation. Thereby, brominations and iodinations of electron-rich and electron-deficient benzamides were ach
Wang, Lianhui,Ackermann, Lutz
supporting information
p. 1083 - 1085
(2014/01/17)
N-tetrahydrofurfuryl-3,5-dimethylbenzamide
This application is directed to novel compounds useful as insect repellents. The compounds of this invention have the following generic formula: SPC1 Wherein R is selected from the group consisting of hydrogen, alkyl, alkoxyalkyl, alkenyl, and cyanoalkyl;
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(2008/06/13)
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