89291-23-6Relevant articles and documents
Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts
Jayaraman, Arumugam,Misal Castro, Luis C.,Fontaine, Frédéric-Georges
supporting information, p. 1489 - 1499 (2018/10/26)
A practical and scalable metal-free catalytic method for the borylation and borylative dearomatization of heteroarenes has been developed. This synthetic method uses inexpensive and conveniently synthesizable bench-stable precatalysts of the form 1-NHR2-2-BF3-C6H4, commercially and synthetically accessible heteroarenes as substrates, and pinacolborane as the borylation reagent. The preparation of several borylated heterocycles on 2 and 50 g scales was achieved under solvent-free conditions without the use of Schlenk techniques or a glovebox. A kilogram-scale borylation of one of the heteroarene substrates was also achieved using this cost-effective green methodology to exemplify the fact that our methodology can be conveniently implemented in fine chemical industries.
FUSED RING PYRIMIDINE COMPOUND, INTERMEDIATE, AND PREPARATION METHOD, COMPOSITION AND USE THEREOF
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Paragraph 0465-0466, (2018/08/12)
Disclosed area fused ring pyrimidine compound, and an intermediate, a preparation method, a composition and a use thereof. The fused ring pyrimidine compound is a compound as shown in formula I, a tautomer, an enantiomer, a diastereoisomer, a pharmaceutically acceptable salt, a metabolite, a metabolic precursor or a prodrug thereof, wherein the above-mentioned compound is used for the preparation of a medicine for preventing, remitting or treating one or more of immune system diseases, autoimmune diseases, cell proliferative diseases, allergic disorders and cardiovascular diseases, and the compound has a strong inhibitory effect on the Janues kinase, FGFR kinase, FLT3 kinase and Src family kinase.
Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp3)?H Addition to Carbon–Carbon Double Bonds
Torigoe, Takeru,Ohmura, Toshimichi,Suginome, Michinori
supporting information, p. 14272 - 14276 (2017/10/23)
Highly enantioselective cycloisomerization of N-methylanilines, bearing o-alkenyl groups, into indolines is established. An iridium catalyst bearing a bidentate chiral diphosphine effectively promotes the intramolecular addition of the C(sp3)?H bond across a carbon–carbon double bond in a highly enantioselective fashion. The reaction gives indolines bearing a quaternary stereogenic carbon center at the 3-position. The reaction mechanism involves rate-determining oxidative addition of the N-methyl C?H bond, followed by intramolecular carboiridation and subsequent reductive elimination.
Axial chirality control during suzuki-miyaura cross-coupling reactions: The tert-Butylsulfinyl group as an efficient chiral auxiliary
Colobert, Francoise,Valdivia, Victoria,Choppin, Sabine,Leroux, Frederic R.,Fernandez, Inmaculada,Alvarez, Eleuterio,Khiar, Noureddine
supporting information; experimental part, p. 5130 - 5133 (2009/12/28)
An efficient route to a new family of axially chiral biaryl ligands by a Suzuki-Miyaura cross-coupling reaction between ortho,ortho'-disubstituted aryl iodides bearing in ortho position a tert-butyl or p-tolylsulfinyl group and ortho-substituted phenyl boronic acids or esters is described. The comparison between the t-BuSO and p-TolSO groups as chiral controllers is reported. The modularity of the approach is demonstrated by the preparation of a variety of enantiopure axially chiral mixed S/N and S/P ligands.
Novel extensions of the tert-amino effect: Formation of phenanthridines and diarene-fused azocines from ortho-ortho′-functionalized biaryls
Polonka-Bálint, ágnes,Saraceno, Caterina,Ludányi, Krisztina,Bényei, Attila,Mátyus, Péter
scheme or table, p. 2846 - 2850 (2009/05/07)
Phenanthridines and azocines fused to two benzene rings or one benzene and one pyridazinone ring, which are otherwise difficult to access, were prepared via two new extensions of the tert-amino effect. The synthetic pathway includes three steps: i) Suzuki reaction of an ortho-functionalized phenylboronic acid with ortho-disubstituted benzenes or pyridazinones; ii) the Knoevenagel condensation reaction of the biaryl aldehydes formed with active methylene compounds to obtain vinyl derivatives or, through their cyclization, phenanthridines via a tert-amino effect; and iii) thermal isomerization of vinyl or phenanthridinium compounds to fused azocines via another type of tert-amino effect. Georg Thieme Verlag Stuttgart.
Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: Discovery of new effective chiral ligands
Bonnaventure, Isabelle,Charette, Andre B.
, p. 6330 - 6340 (2008/12/22)
(Chemical Equation Presented) The hemilabile ligand Me-DuPHOS(O) 2 has proven to be a successful ligand for the copper-catalyzed addition of diethylzinc to N-phosphinoylimines. The corresponding α-chiral amines were obtained in high yields (80-98%) and enantiomeric ratios (19.0:1 to 99.0:1 er). Furthermore, this Cu?2 catalytic system has been shown to be effective in the addition of diethylzinc to nitroalkenes and in the reduction of β,β-disubstituted vinyl phenyl sulfones. This paper describes a general structure/selectivity study in which the three ligand subunits (chiral phospholane-linker-labile coordinating group (Z)) are systematically modified and tested in the copper-catalyzed addition of diethylzinc to the N-phosphinoylimine 1 derived from benzaldehyde. This study led to the discovery of a new class of effective chiral ligands that combine a chiral phospholane unit and an achiral phosphine oxide.
ARYLBORONIC ACIDS WITH INTRAMOLECULAR B-N INTERACTION: CONVENIENT SYNTHESIS THROUGH ortho-LITHIATION OF SUBSTITUTED BENZYLAMINES
Lauer, Manfred,Wulff, Guenter
, p. 1 - 10 (2007/10/02)
Ortho-lithiation of N,N-dimethylbenzylamine and reaction with trimethylborate gave the corresponding boronic acid in good yields.The reaction was extended to the synthesis of various aromatic boron compounds with nitrogen-containing substituents in the ortho-position, including a chiral boroxin prepared from (S)-N,N-dimethyl-1-phenylethylamine.From N-Methyl-benzylamine a stable boronium salt was obtained under certain conditions.The spectra of the newly synthesized compounds are discussed.Intramolecular B-N interaction is established by 11B NMR spectroscopy.
