101089-83-2Relevant academic research and scientific papers
One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
Watanabe, Toshiaki,Ueda, Satoshi,Inuki, Shinsuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
, p. 4516 - 4518 (2007)
One-pot N-arylation and oxidative coupling can be promoted by a common palladium catalyst in the presence of appropriate additives: palladium-catalyzed N-arylation of anilines with aryl triflates under the standard conditions followed by addition of acetic acid under oxygen or air atmosphere afforded various types of functionalized carbazoles in good to excellent yields. The Royal Society of Chemistry.
Amination with Pd-NHC complexes: Rate and computational studies involving substituted aniline substrates
Hoi, Ka Hou,Calimsiz, Selcuk,Froese, Robert D. J.,Hopkinson, Alan C.,Organ, Michael G.
, p. 145 - 151 (2012)
The amination of aryl chlorides with various aniline derivatives using the N-heterocyclic carbene-based Pd complexes Pd-PEPPSI-IPr and Pd-PEPPSI-IPent (PEPPSI=pyridine, enhanced precatalyst, preparation, stabilization, and initiation; IPr=diisopropylphenylimidazolium derivative; IPent= diisopentylphenylimidazolium derivative) has been studied. Rate studies have shown a reliance on the aryl chloride to be electron poor, although oxidative addition is not rate limiting. Anilines couple best when they are electron rich, which would seem to discount deprotonation of the intermediate metal ammonium complex as being rate limiting in favour of reductive elimination. In previous studies with secondary amines using PEPPSI complexes, deprotonation was proposed to be the slow step in the cycle. These experimental findings relating to mechanism were corroborated by computation. Pd-PEPPSI-IPr and the more hindered Pd-PEPPSI-IPent catalysts were used to couple deactivated aryl chlorides with electron poor anilines; while the IPr catalysis was sluggish, the IPent catalyst performed extremely well, again showing the high reactivity of this broadly useful catalyst. Copyright
Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines
Guan, Xinyu,Zhu, Haoran,Driver, Tom G.
, p. 12417 - 12422 (2021/10/12)
The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C-NAr bond formation of the nitrosoarene with the aryl boronic acid.
Sodium Butylated Hydroxytoluene: A Functional Group Tolerant, Eco-Friendly Base for Solvent-Free, Pd-Catalysed Amination
Semeniuchenko, Volodymyr,Braje, Wilfried M.,Organ, Michael G.
supporting information, p. 12535 - 12539 (2021/08/03)
NaBHT (sodium 2,6-di-tert-butyl-4-methylphenolate), a strong, but hindered and lipophilic base, has been effectively paired with similarly lipophilic, high-reactivity Pd-NHC (N-heterocyclic carbene) catalysts to produce an ideal combination for performing
A Tetraarylpyrrole-Based Phosphine Ligand for the Palladium-Catalyzed Amination of Aryl Chlorides
Sai, Masahiro
supporting information, p. 5422 - 5428 (2021/10/08)
A tetraarylpyrrole-based phosphine ligand L1 in combination with Pd(dba)2 provided a catalyst for the Buchwald-Hartwig amination reaction. A variety of amines were rapidly coupled with aryl chlorides at a Pd loading of 0.5 mol%. The selective monoarylation of aliphatic primary amines was achieved in the presence of 0.8 equiv. water. Comparison experiments were also conducted, which revealed that the catalytic activity of L1 is superior to representative phosphine ligands in the Pd-catalyzed C?N coupling of various amines. (Figure presented.).
Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines
Akram, Manjur O.,Das, Avishek,Chakrabarty, Indradweep,Patil, Nitin T.
supporting information, p. 8101 - 8105 (2019/10/11)
The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.
PHOSPHINE COMPOUND, CROSSLINKED COMPOSITION, AND MANUFACTURING METHOD OF AROMATIC AMINE COMPOUND
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Paragraph 0044-0046; 0054-0056, (2019/12/25)
PROBLEM TO BE SOLVED: To provide a phosphine compound capable of constituting a transition metal complex excellent in reaction speed and selectivity as a catalyst. SOLUTION: There is provided a phosphine compound represented by the formula (I). In the formula Ar represents each independently an aryl group which may be substituted, R1 represents each independently a linear, branched or cyclic alkyl group, R2 represents each independently a linear, branched or cyclic alkyl group, alkoxy group or aryl group which may be substituted, or neighboring 2 R2 are bound each other to form a ring, and n represents an integer of 0 to 4. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
Discovery of carbazole carboxamides as novel RORγt inverse agonists
Huang, Yafei,Yu, Mingcheng,Sun, Nannan,Tang, Ting,Yu, Fazhi,Song, Xiaoxia,Xie, Qiong,Fu, Wei,Shao, Liming,Wang, Yonghui
, p. 465 - 476 (2018/02/28)
A novel series of carbazole carboxamides was discovered as potent RORγt inverse agonists using a scaffold hybridization strategy. Structure-activity relationship exploration on the amide linker, carbazole ring and arylsulfone moiety of the hybrid amide 3a led to identification of potent RORγt inverse agonists. Compound 6c was found to have a good RORγt activity with an IC50 of 58.5 nM in FRET assay, and reasonable inhibitory activity in mouse Th17 cell differentiation assay (58.8% inhibition at 0.3 μM). The binding mode of carbazole carboxamides in RORγt ligand binding domain was discussed.
Effects of solvent and base on the palladium-catalyzed amination: PdCl 2(Ph3P)2/Ph3P-catalyzed selective arylation of primary anilines with aryl bromides
Cai, Liangzhen,Qian, Xuanying,Song, Wenjing,Liu, Taoping,Tao, Xiaochun,Li, Wanfang,Xie, Xiaomin
, p. 4754 - 4759 (2014/06/24)
A readily accessible catalytic system, PdCl2(Ph 3P)2/Ph3P, was developed for the selective arylation of primary anilines with aryl bromides. The strong influence of solvents and bases on the catalytic activity was observed. In refluxing o-xylene, triphenylphosphine shows high efficiency for Pd-catalyzed intermolecular amination reactions. By changing the bases, mono- and diarylation of primary amines could be selectively achieved in high yields. Moreover, the catalytic system showed good toleration for the steric hindrance of anilines. A series of N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′- diamines, important intermediates of OLED hole transport materials, were synthesized facilely via coupling reactions between 4,4′-diaminobiphenyls and aryl bromides.
Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N -phenyl-aminobenzoates and their structure-activity relationships
Adeniji, Adegoke O.,Twenter, Barry M.,Byrns, Michael C.,Jin, Yi,Chen, Mo,Winkler, Jeffrey D.,Penning, Trevor M.
supporting information; experimental part, p. 2311 - 2323 (2012/05/04)
Aldo-keto reductase 1C3 (AKR1C3; type 5 17β-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5α-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of 5α-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.
