3400-31-5Relevant academic research and scientific papers
The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)
Cao, Chengyao Kimmy,Chen, Chao,Ge, Chenxin,Niu, Yaru,Qu, Hongmei
supporting information, (2021/10/01)
Herein, we report a simple and efficient method for the direct installation of chlorodifluoroethyl group onto aromatic molecules of various aromatic amides with a new 2-chloro,2,2-difluoroethyl(mesityl)iodonium salt (CDFI). Moreover, the chlorodifluoroeth
Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones
Feng, Xiaoming,Hu, Xinyue,Lin, Lili,Wang, Kaixuan,Xu, Chaoran,Zhou, Yuqiao
supporting information, p. 8917 - 8920 (2021/09/10)
An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.
Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines
Gim, Hyo Jin,Jung, Michael E.
supporting information, p. 2548 - 2552 (2019/06/08)
Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N -methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.
Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes
Li, Ze-Lin,Wu, Peng-Yu,Cai, Chun
supporting information, p. 3462 - 3468 (2019/02/25)
A straightforward Ni(ii)-catalyzed general strategy was developed for the ortho-halogenation of electron-deficient arenes with easily available halogenating reagents N-halosuccinimides (NXS; X = Br, Cl and I). The transformation was highly regioselective and a wide substrate scope and functional group tolerance were observed. This discovery could be of great significance for the selective halogenation of amides, benzoic esters and other substances with guiding groups. Mechanistic investigations were also described.
Palladium-Catalyzed Direct C-H Trifluoroethylation of Aromatic Amides
Maraswami, Manikantha,Pankajakshan, Sreekumar,Chen, Gang,Loh, Teck-Peng
supporting information, p. 4223 - 4226 (2017/08/23)
A simple and direct C-H trifluoroethylation of aromatic amides has been developed. The protocol is applicable to a variety of aromatic amides, including ones derived from amino acids. The developed method can be used for further modifications of peptides. Preliminary mechanistic studies have been done by isolating the reaction intermediate.
Ru(II)-Catalyzed C-H Activation: Amide-Directed 1,4-Addition of the Ortho C-H Bond to Maleimides
Keshri, Puspam,Bettadapur, Kiran R.,Lanke, Veeranjaneyulu,Prabhu, Kandikere Ramaiah
, p. 6056 - 6065 (2016/07/26)
Maleimide has been used as a selective coupling partner to generate conjugate addition products exclusively. The typical Heck-type oxidative coupling that occurs when alkenes are used is avoided by choosing maleimide as an alkene, which cannot undergo β-hydride elimination due to the unavailability of a syn-periplanar β-hydrogen atom. The amide nitrogen, which is notorious for undergoing tandem reactions to generate spirocyclic or annulation products under cross-coupling conditions, remains innocent in this report. Along with the substrate scope, a robustness screen has been performed to analyze the performance of amide as a directing group in the presence of other directing groups and also to examine the tolerance of the reaction conditions for other frequently encountered functional groups.
Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines
Lamers, Philip,Priebbenow, Daniel L.,Bolm, Carsten
, p. 5594 - 5602 (2015/09/01)
As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine. The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.
Bis-aryl triazoles as selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1
Aster, Susan D.,Graham, Donald W.,Kharbanda, Divya,Patel, Gool,Ponpipom, Mitree,Santorelli, Gina M.,Szymonifka, Michael J.,Mundt, Steven S.,Shah, Kashmira,Springer, Marty S.,Thieringer, Rolf,Hermanowski-Vosatka, Anne,Wright, Samuel D.,Xiao, Jianying,Zokian, Hratch,Balkovec, James M.
, p. 2799 - 2804 (2008/12/21)
3-Aryl-5-phenyl-(1,2,4)-triazoles were identified as selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). They are active in both in vitro and an in vivo mouse pharmacodynamic (PD) model. The synthesis and structure activity relatio
Room-temperature debenzylation of N-benzylcarboxamides by N-bromosuccinimide
Kuang, Liping,Zhou, Jing,Chen, Sheng,Ding, Ke
, p. 3129 - 3134 (2008/03/28)
A simple and highly efficient method has been developed with which to cleave the N-benzyl group on N-mono- or disubstituted carboxamides using N-bromosuccinimide (NBS) at room temperature. All the 31 substrates examined showed moderate to excellent deprotection yields. Our study also indicated that the debenzylation may involve an oxygen/light initiated free radical mechanism. Georg Thieme Verlag Stuttgart.
Efficient Beckmann rearrangement and dehydration of oximes via phosphonate intermediates
Sardarian,Shahsavari-Fard,Shahsavari,Ebrahimi
, p. 2639 - 2643 (2007/10/03)
Under mild conditions, conversion of a variety of ketoximes and aldoximes to their corresponding amides and nitriles proceeded in the presence of diethyl chlorophosphate with excellent yields.
