37459-58-8Relevant academic research and scientific papers
Exploiting the Bis-Nucleophilicity of α-Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides
Dumas, Aaron M.,Sieradzki, Adrian J.,Donnelly, Liam J.
, p. 1848 - 1851 (2016/05/19)
α-Aminoboronate salts are interesting examples of heteroatomic species containing adjacent nucleophilic centers. We have developed an acylation/arylation reaction using 2-bromobenzoyl chlorides as bis-electrophiles that harnesses the nucleophilicity of both positions, leading to isoindolinones. The reactions proceed under mild conditions via an intramolecular, Cu-catalyzed sp3-sp2 coupling, giving products in up to 95% yield. These conditions enable arylation of α,α-disubstituted aminoboronates, which are difficult to accomplish using methods based on less abundant and more expensive transition metals.
Copper-catalyzed C(sp3)-oh cleavage with concomitant c-c coupling: Synthesis of 3-substituted isoindolinones
Rao, H. Surya Prakash,Rao, A. Veera Bhadra
, p. 1506 - 1516 (2015/02/19)
Copper(II) trifluoromethanesulfonate (Cu(OTf)2) efficiently catalyzes the C-C coupling of 3-hydoxyisoindolinones with a variety of aryl-, heteroaryl-, and alkenylboronic acids to furnish C(3) aryl-, heteroaryl-, and alkenyl-substituted isoindolinones. The coupling reactions work smoothly in 1,2-dicholoroethane (DCE) reflux, to effect both inter- and intramolecular versions. This is the first report on C(sp3)-OH cleavage with concomitant C-C coupling. The photolabile 2-nitrobenzyl protecting group is most appropriate for promotion of the coupling reaction and for deprotection. The tetracyclic ring motif of the alkaloid neuvamine was prepared by applying the newly developed copper-catalyzed C-C coupling.
TfOH-catalyzed synthesis of 3-aryl isoindolinones via a tandem reaction
Hu, Jiaxing,Qin, Hua-Li,Xu, Wengang,Li, Junli,Zhang, Fanglin,Zheng, Hua
supporting information, p. 15780 - 15783 (2015/01/08)
A convenient metal-free method for the synthesis of 3-aryl isoindolinones via TfOH catalyzed aromatic C-H functionalization of electron-rich arenes with 2-formylbenzonitriles is developed. This process provided a new efficient strategy for the synthesis of isoindolinone derivatives in good to high yields and regioselectivities by forming two bonds.
N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
Augner, Daniel,Gerbino, Dario C.,Slavov, Nikolay,Neudoerfl, Joerg-Martin,Schmalz, Hans-Guenther
supporting information; experimental part, p. 5374 - 5377 (2011/12/03)
A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild
Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXVIII. 3-Alkoxy-1H-isoindole mit Substituenten am 5-Ring - Heterocycliche Imidsaeureester mit fixierter benzoider Struktur.
Kreher, Richard P.,Hennige, Hans,Konrad, Michael,Uhrig, Juergen,Clemens, Andrea
, p. 809 - 828 (2007/10/02)
3-Alkoxy-1H-isoindoles bearing substituents at the five-membered ring have been synthesized starting with substituted isoindoline-1-ones via regiospecific O-alkylation with trialkyl oxonium tetrafluoroborates or alkyl trifluoromethanesulfonates and subsequent NH-deprotonation.The dependence of spectroscopic properties on the substituents has been investigated.The heterocyclic imidates exist exclusively in the benzenoid 1H-structure; the tautomeric o-quinonoid 2H-form cannot be detected by spectroscopic means.
