274258-85-4Relevant academic research and scientific papers
A chemoselective and scalable transfer hydrogenation of aryl imines by rapid continuous flow photoredox catalysis
Pilkington, Rowan L.,Rossouw, Nikolai P.,Van As, Dean J.,Polyzos, Anastasios
, p. 823 - 827 (2019)
The chemoselective reduction of diaryl imines in the presence of competitively reducible groups is uniquely accessed through precise control of reaction and irradiation time by continuous flow visible light photoredox catalysis. The method enables the mild and efficient transfer hydrogenation of diaryl imines in the presence of sensitive functionality including halides, ester, ketone, and cyano groups. The flow protocol is efficient, rapid (>98% conversion within 9 min) and readily scaled to deliver multigram quantities of amine products in high purity.
Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines
He, Feifei,Empel, Claire,Koenigs, Rene M.
, p. 6719 - 6723 (2021/09/13)
Herein, we report on the N-H functionalization reaction of primary and secondary anilines with diaryldiazoalkanes using simple AgPF6 as catalyst. We demonstrated broad applicability in the reaction of diaryldiazoalkanes with different anilines (31 examples, up to 97% yield). Furthermore, we propose a possible reaction mechanism for the N-H functionalization.
Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow
Van As, Dean J.,Connell, Timothy U.,Brzozowski, Martin,Scully, Andrew D.,Polyzos, Anastasios
supporting information, p. 905 - 908 (2018/02/22)
A visible-light photocalytic method for the chemoselective transfer hydrogenation of imines in batch and continuous flow is described. The reaction utilizes Et3N as both hydrogen source and single-electron donor, enabling the selective reduction of imines derived from diarylketimines containing other reducible functional groups including nitriles, halides, esters, and ketones. The dual role of Et3N was confirmed by fluorescence quenching measurements, transient absorption spectroscopy, and deuterium-labeling studies. Continuous-flow processing facilitates straightforward scale-up of the reaction.
Correction to: Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow (Organic Letters (2018) 20:4 (905-908) DOI: 10.1021/acs.orglett.7b03565)
Van As, Dean J.,Connell, Timothy U.,Brzozowski, Martin,Scully, Andrew D.,Polyzos, Anastasios
, p. 4392 - 4392 (2018/07/29)
Sections of Schemes 2 and 4 were omitted in error during the production process. The complete versions of Schemes 2 and 4 are shown below.(Figure Persented).Scheme 2 is corrected as follows:.
Iron-catalyzed C-C bond cleavage and C-N bond formation
Li, Wenjuan,Zheng, Xiaojian,Li, Zhiping
, p. 181 - 190 (2013/03/13)
A novel approach for C-N bond formation was developed by iron-catalyzed C-C bond cleavage. Anilines and sulfonamides reacted smoothly with 2-substituted 1,3-diphenylpropane-1,3-diones to afford N-alkylation products, in which the 1,3-dicarbonyl group acts as a leaving group in the presence of an iron catalyst. The reversible C-C bond cleavage plays a driving force to give the thermodynamically stable products. The method is complementary to the previous methods for C-N bond formation. Copyright
