37772-00-2Relevant academic research and scientific papers
Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation
Cardinale, Luana,Schmotz, Mattis-Ole W. S.,Konev, Mikhail O.,Jacobi von Wangelin, Axel
supporting information, p. 506 - 510 (2022/01/20)
An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.
Catalytic Asymmetric Reduction of α-Trifluoromethylated Imines with Catecholborane by BINOL-Derived Boro-phosphates
He, Hualing,Tang, Xiaoxue,Cao, Yang,Antilla, Jon C.
, p. 4336 - 4345 (2021/03/01)
A catalytic enantioselective reduction of α-trifluoromethylated imines by a BINOL-derived boro-phosphate employing catecholborane as hydride source has been developed. This method provides an efficient route to prepare synthetically useful chiral α-triflu
H2 Activation by Non-Transition-Metal Systems: Hydrogenation of Aldimines and Ketimines with LiN(SiMe3)2
Elliott, Daniel C.,Marti, Alex,Mauleón, Pablo,Pfaltz, Andreas
supporting information, p. 1918 - 1922 (2019/01/16)
In recent years, H2 activation at non-transition-metal centers has met with increasing attention. Here, a system in which H2 is activated and transferred to aldimines and ketimines using substoichiometric amounts of lithium bis(trimethylsilyl)amide is reported. Notably, the reaction tolerates the presence of acidic protons in the α-position. Mechanistic investigations indicated that the reaction proceeds via a lithium hydride intermediate as the actual reductant.
Rhodium-Catalyzed C=N Bond Formation through a Rebound Hydrolysis Mechanism and Application in β-Lactam Synthesis
Chen, Long,Zhang, Linxing,Shao, Ying,Xu, Guangyang,Zhang, Xinhao,Tang, Shengbiao,Sun, Jiangtao
supporting information, p. 4124 - 4127 (2019/06/08)
A rhodium-catalyzed reaction of N-hydroxyanilines with diazo compounds to produce α-imino esters was developed. Distinct from the commonly accepted 1,2-H transfer for normal X-H insertion reactions, density functional theory calculations indicate that this transformation proceeds via a novel rebound hydrolysis mechanism. Furthermore, a three-component reaction was explored to synthesize highly functionalized β-lactams in good yields and diastereoselectivities.
Nickel-catalyzed dehydrogenative cross-coupling: Direct transformation of aldehydes into esters and amides
Whittaker, Aaron M.,Dong, Vy M.
supporting information, p. 1312 - 1315 (2015/01/30)
By exploring a new mode of nickel-catalyzed cross-coupling, a method to directly transform both aromatic and aliphatic aldehydes into either esters or amides has been developed. The success of this oxidative coupling depends on the appropriate choice of catalyst and organic oxidant, including the use of either α,α,α-trifluoroacetophenone or excess aldehyde. Mechanistic data that supports a catalytic cycle involving oxidative addition into the aldehyde C-H bond is also presented.
Solid fly-ash:h2so4 catalyzed microwave assisted solvent-free condensation:synthesis of some trifluoromethyl-imines
Thirunarayanan,Mayavel,Thirumurthy,Vanangamudi,Sekar,Lakshmanan
, p. 2231 - 2234 (2014/03/21)
Good yield of trifluoromethyl-imines have been synthesized by Fly-ash:H2SO4 catalyzed condensation of anilines and phenyl trifluoromethyl ketone in microwave irradiation under solvent free conditions.
Synthesis of N-aryl trifluoromethylarylketoimines by palladium-catalyzed Suzuki coupling reaction of N-aryltrifluoroacetimidoyl chlorides with aryl boronic acids
Li, Chun-Lin,Chen, Mu-Wang,Zhang, Xing-Guo
experimental part, p. 856 - 860 (2010/09/05)
A highly efficient Suzuki reaction between N-aryltrifluoroacetimidoyl chlorides and aryl boronic acids using Pd(PPh3)4 as a catalyst has been developed. This route allows for selective synthesis of N-aryl trifluoromethylarylketoimines in high yields under mild reaction conditions.
Acyclic amides as estrogen receptor ligands: Synthesis, binding, activity and receptor interaction
Stauffer, Shaun R.,Sun, Jun,Katzenellenbogen, Benita S.,Katzenellenbogen, John A.
, p. 1293 - 1316 (2007/10/03)
We have prepared a series of bisphenolic amides that mimic bibenzyl and homobibenzyl motifs commonly found as substructures in ligands for the estrogen receptor (ER). Representative members were prepared from three classes: N-phenyl benzamides, N-phenyl acetamides, and N-benzyl benzamides; in some cases the corresponding thiocarboxamides and sulfonamides were also prepared. Of these three classes, the N-phenyl benzamides had the highest affinity for ER, the N-phenyl acetamides had lower, and the N-benzyl benzamides were prone to fragmentation via a quinone methide intermediate. In the N-phenyl benzamide series, the highest affinity analogues had bulky N-substituents; a CF3 group, in particular, conferred high affinity. The thiocarboxamides bound better than the corresponding carboxamides and these bound better than the corresponding sulfonamides. Binding affinity comparisons suggest that the p-hydroxy group on the benzoate ring, which contributes most to the binding, is playing the role of the phenolic hydroxyl of estradiol. Computational studies and NMR and X-ray crystallographic analysis indicate that the two anilide systems studied have a strong preference for the s-cis or exo amide conformation, which places the two aromatic rings in a syn orientation. We used this structural template, together with the X-ray structure of the ER ligand binding domain, to elaborate an additional hydrogen bonding site on a benzamide system that elevated receptor binding further. When assayed on the individual ER subtypes, ERα and ERβ, these compounds show modest binding affinity preference for ERα. In a reporter gene transfection assay of transcriptional activity, the amides generally have full to nearly full agonist character on ERα, but have moderate to full antagonist character on ERβ. One high affinity carboxamide is 500-fold more potent as an agonist on ERα than on ERβ. This work illustrates that ER ligands having simple amide core structures can be readily prepared, but that high affinity binding requires an appropriate distribution of bulk, polarity, and functionality. The strong conformational preference of the core anilide function in all of these ligands defines a rather rigid geometry for further structural and functional expansion of these series. Copyright (C) 2000 Elsevier Science Ltd.
