6709-42-8Relevant academic research and scientific papers
Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines
He, Feifei,Empel, Claire,Koenigs, Rene M.
supporting information, 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.
Implication of a Silyl Cobalt Dihydride Complex as a Useful Catalyst for the Hydrosilylation of Imines
Barbazanges, Marion,Bories, Cassandre C.,Derat, Etienne,Petit, Marc
, p. 14262 - 14273 (2021/11/27)
Here, we describe the formation and use of silyl cobalt (III) dihydride complexes as powerful catalysts for the hydrosilylation of a variety of imines starting from a low-valent well-defined cobalt (I) complex. The reaction is efficient at low catalyst loadings with a diverse range of imines bearing various protecting groups, as well as aliphatic ketimines and quinoline. Kinetics, DFT calculations, NMR spectroscopic studies, deuteration experiments, and X-ray diffraction analyses allowed us to propose a catalytic cycle based on silyl dihydrocobalt (III) complexes performing a hydrocobaltation.
Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and ortho C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols
Meng, Shan-Shui,Tang, Xiaowen,Luo, Xiang,Wu, Ruibo,Zhao, Jun-Ling,Chan, Albert S. C.
, p. 8397 - 8403 (2019/09/03)
An unprecedented protocol for the efficient and highly chemoselective alkylation of unprotected arylamines using alcohols catalyzed by B(C6F5)3 has been developed. The reaction gives N-alkylated products and ortho C-alkylated products in different solvents in good chemoselectivities and yields. Control experiments and DFT calculations indicated that the borane underwent alcohol/arylamine exchange to ensure catalytic activity, and a possible mechanism involving a carbocation is proposed.
General synthesis of N-Alkylation of amines with secondary alcohols via hydrogen autotransfer
Subaramanian, Murugan,Midya, Siba P.,Ramar, Palmurukan M.,Balaraman, Ekambaram
supporting information, p. 8899 - 8903 (2019/11/14)
Direct catalytic N-alkylation of amines with secondary alcohols via hydrogen autotransfer (HA) strategy is very challenging and has been scarcely reported, even under precious metal catalysis. Herein, an efficient N-alkylation of amines, including benzyla
Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex
Aiolfi, Francesco,Bai, Xishan,Cettolin, Mattia,Dal Corso, Alberto,Gennari, Cesare,Piarulli, Umberto,Pignataro, Luca
, p. 3545 - 3555 (2019/09/09)
Thanks to a highly active catalyst, the scope of the (cyclopentadienone)iron complex-promoted 'hydrogen-borrowing' (HB) amination has been expanded to secondary alcohols, which had previously been reported to react only in the presence of large amounts of co-catalysts. A range of cyclic and acyclic secondary alcohols were reacted with aromatic and aliphatic amines giving fair to excellent yields of the substitution products. The catalyst was also able to promote the cyclization of diols bearing a secondary alcohol group with primary amines to generate saturated N-heterocycles.
Method for catalyzing benzyl alcohol compound to be aminated
-
Paragraph 0031; 0032; 0033, (2019/01/14)
The invention belongs to the field of organic synthesis, and discloses a method for catalyzing a benzyl alcohol compound to be aminated. The method comprises the steps that the benzyl alcohol compoundand an aniline compound are mixed, a solvent and a cata
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:.
Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water
Wang, Rui,Ma, Mengyue,Gong, Xu,Panetti, Grace B.,Fan, Xinyuan,Walsh, Patrick J.
supporting information, p. 2433 - 2436 (2018/04/27)
A novel carbanionic reactivity of imines mediated by photoredox catalysis is demonstrated. The umpolung imine reactivity is exemplified by proton abstraction from water as a key step in the reduction of benzophenone ketimines to amines (up to 98% yield). Deuterium is introduced into amines efficiently using D2O as an inexpensive deuterium source (≥95% D ratio). The mechanism of this unusual transformation is probed.
Efficient Synthesis of Amines by Iron-Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination
Facchini, Sofia Vailati,Cettolin, Mattia,Bai, Xishan,Casamassima, Giuseppe,Pignataro, Luca,Gennari, Cesare,Piarulli, Umberto
supporting information, p. 1054 - 1059 (2018/01/27)
Here we report the catalytic transfer hydrogenation (CTH) of non-activated imines promoted by a Fe-catalyst in the absence of Lewis acid co-catalysts. Use of the (cyclopentadienone)iron complex 1, which is much more active than the classical ‘Kn?lker complex’ 2, allowed to reduce a number of N-aryl and N-alkyl imines in very good yields using iPrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe-complex as the only catalyst has little precedents. Based on this methodology, we developed a one-pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates. (Figure presented.).
