877264-43-2Relevant academic research and scientific papers
Pd(II)-Catalyzed Synthesis of Benzocyclobutenes by β-Methylene-Selective C(sp3)-H Arylation with a Transient Directing Group
Chen, Xiangyang,Hoskin, John F.,Houk, K. N.,Provencher, Philip A.,Sorensen, Erik J.,Wong, Jonathan J.,Yu, Jin-Quan
supporting information, p. 20035 - 20041 (2021/12/09)
Methylene-selective C-H functionalization is a significant hurdle that remains to be addressed in the field of Pd(II) catalysis. We report a Pd(II)-catalyzed synthesis of benzocyclobutenes by methylene-selective C(sp3)-H arylation of ketones. The reaction utilizes glycine as a transient directing group and a 2-pyridone ligand, which may govern the methylene selectivity by making intimate molecular associations with the substrate during concerted metalation-deprotonation. This reaction is shown to be highly selective for intramolecular methylene C(sp3)-H arylation, thus enabling sequential C(sp3)-H functionalization.
MACROCYCLIC COMPOUNDS USEFUL AS CHITINASE INHIBITORS
-
Paragraph 0128; 0165-0166; 169, (2021/07/29)
The present invention relates to macrocyclic compounds of formula (I) and their use as chitinase inhibitors as well as to pharmaceutical compositions and methods of preparation thereof. The compounds can in particular be used in the treatment, prevention and/or amelioration of asthma.
One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts
Caspers, Lucien D.,Spils, Julian,Damrath, Mattis,Lork, Enno,Nachtsheim, Boris J.
, p. 9161 - 9178 (2020/08/14)
Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Br?nsted acids enable the effective Friedel-Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.
Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
supporting information, p. 14330 - 14334 (2020/10/12)
A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes
He, Jun,Xue, Yuhang,Han, Bo,Zhang, Chunzhu,Wang, You,Zhu, Shaolin
supporting information, p. 2328 - 2332 (2020/01/08)
Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis.
CuSO4-Catalyzed dual annulation to synthesize O, S or N-containing tetracyclic heteroacenes
Kang, Yan-Biao,Qu, Jian-Ping,Shan, Xiang-Huan,Yang, Bo
supporting information, p. 4063 - 4066 (2020/04/20)
In this work, CuSO4 is utilized as a practical redox catalyst for tandem dual annulation in the synthesis of indole-fused tetracyclic heteroacenes, which are important skeletons in both medicinal chemistry and materials chemistry. The preparation of such skeletons in a convenient and efficient manner is in high demand. This method realizes the modular synthesis of benzofuro-, benzothieno-, and indoloindoles from abundant feedstocks such as 2-halobenzyl halides and nitrile derivatives in up to 99% yields, providing a rapid access to diverse indole-fused heteroacenes with biological or optoelectronic properties.
Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation
Whyte, Andrew,Olson, Maxwell E.,Lautens, Mark
supporting information, p. 345 - 348 (2018/01/27)
A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and are present in bioactive molecules. This work highlights the challenge of competing intra- vs intermolecular palladium-catalyzed processes.
Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes
Li, Bin,Chao, Zengyin,Li, Chunyu,Gu, Zhenhua
supporting information, p. 9400 - 9403 (2018/07/30)
A Cu-catalyzed enantioselective desymmetrizing ring-opening reaction of six-membered cyclic diaryliodonium salts with carboxylic acids or thioacids is reported for the facile access to chiral diarylmethanes. A Cu/[cyclopropyl bis(oxazoline)] catalyst well
F- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF3-Substituted Indenes
Tang, Hai-Jun,Zhang, Yu-Feng,Jiang, Yi-Wen,Feng, Chao
, p. 5190 - 5193 (2018/09/12)
An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.
Intramolecular Pd-Catalyzed Arylation of 1-Amidosugars: A New Route to N-Glycosyl Quinolin-2-ones
Luong, Thi Thanh Huyen,Brion, Jean-Daniel,Lescop, Ewen,Alami, Mouad,Messaoudi, Samir
supporting information, p. 2126 - 2129 (2016/06/01)
The synthesis of N-glycosylated quinolin-2-ones via an intramolecular N-arylation of glycosylamides is reported. The coupling involves the use of only Pd(OAc)2 as the catalyst and nBu4NOAc as the base in 1,4-dioxane. This versatile approach allows the synthesis of various N-glycosylated quinolin-2-ones with exclusive α or β selectivity.
