- Enantioselective Synthesis of N–C Axially Chiral Compounds by Cu-Catalyzed Atroposelective Aryl Amination
-
N?C axially chiral compounds have emerged recently as appealing motifs for drug design. However, the enantioselective synthesis of such molecules is still poorly developed and surprisingly no metal-catalyzed atroposelective N-arylations have been describe
- Choppin, Sabine,Colobert, Fran?oise,Delso, Isabel,Frey, Johanna,Malekafzali, Alaleh,Wencel-Delord, Joanna
-
-
Read Online
- IrIII-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C?H Bonds
-
An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C?H bonds is presented. A wide range of electron-rich and electron-poor substrates undergo the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C?H iodination occurs selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction is performed at room temperature and no inert atmosphere or exclusion of moisture is required. Mechanistic investigations revealed a substrate-dependent reversible C?H activation/protodemetalation step, a substrate-dependent turnover-limiting step, and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction.
- Weis, Erik,Johansson, Magnus J.,Martín-Matute, Belén
-
supporting information
p. 10185 - 10190
(2020/07/31)
-
- Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations
-
The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).
- Boelke, Andreas,Nachtsheim, Boris J.
-
supporting information
p. 184 - 191
(2019/12/11)
-
- Iodolopyrazolium Salts: Synthesis, Derivatizations, and Applications
-
The synthesis of iodolopyrazolium triflates via an oxidative cyclization of 3-(2-iodophenyl)-1H-pyrazoles is described. The reaction is characterized by a broad substrate scope, and various applications of these novel cyclic iodolium salts acting as useful synthetic intermediates are demonstrated, in particular in site-selective ring openings. This was finally applied to generate derivatives of the anti-inflammatory drug celecoxib. Their application as highly active halogen-bond donors is shown as well.
- Boelke, Andreas,Caspers, Lucien D.,Kuczmera, Thomas J.,Lork, Enno,Nachtsheim, Boris J.
-
supporting information
p. 7261 - 7266
(2020/10/05)
-
- SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE
-
Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.
- -
-
Page/Page column 991
(2016/04/10)
-
- Imidazole derivative used as antiviral agent and use thereof in preparation of medicament
-
Disclosed are an antiviral compound and a use thereof in the preparation of a medicament for the treatment of virus infections. Specifically, the present invention relates an imidazole derivative for treating respiratory syncytial virus infection.
- -
-
Paragraph 0335; 0336; 0337
(2016/10/07)
-
- Palladium-catalyzed annulation reactions of methyl o-halobenzoates with azabicyclic alkenes: A general protocol for the construction of benzo[c]phenanthridine derivatives
-
The annulation reaction of methyl o-halobenzoates with azabicyclic alkenes proceeds efficiently to give the corresponding benzo[c]phenanthridine derivatives in good to excellent yields using a developed base-free methodology based on our preliminary studies. Thirty-seven application examples validate the compatibility of the present strategy with different groups, particularly with the electron-deficient ones, that are difficult to access using other traditional methods. In addition, annulation reactions with non-symmetric azabicyclic alkenes are achieved in high regioselectivity.
- Guo, Cui,Huang, Kanglun,Wang, Bo,Xie, Longguang,Xu, Xiaohua
-
p. 17271 - 17280
(2013/09/24)
-
- NAPHTHALENONE COMPOUNDS EXHIBITING PROLYL HYDROXYLASE INHIBITORY ACTIVITY, COMPOSITIONS, AND USES THEREOF
-
Compounds of Formula (I) and Formula (II) are useful as inhibitors of HIF prolyl hydroxylases. Compounds of Formula(I) and Formula (II) have the following structures, where the definitions of the variables are provided herein.
- -
-
Page/Page column 205-206
(2008/12/06)
-
- Ortho-metalation of unprotected 3-bromo and 3-chlorobenzoic acids with hindered lithium dialkylamides
-
Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 °C, lithium 3-chloro/bromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of s
- Gohier, Frederic,Mortier, Jacques
-
p. 2030 - 2033
(2007/10/03)
-