76154-08-0Relevant articles and documents
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
supporting information, (2020/06/17)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
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.).
Decrypting Transition States by Light: Photoisomerization as a Mechanistic Tool in Br?nsted Acid Catalysis
Renzi, Polyssena,Hioe, Johnny,Gschwind, Ruth M.
supporting information, p. 6752 - 6760 (2017/05/29)
Despite the wide applicability of enantioselective Br?nsted acid catalysis, experimental insight into transition states is very rare, and most of the mechanistic knowledge is gained by theoretical calculations. Here, we present an alternative approach (de
MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts
Davaasuren, Bambar,Emwas, Abdul-Hamid,Rothenberger, Alexander
, p. 9609 - 9616 (2017/08/26)
High surface area macroporous chalcogenide aerogels (chalcogels) MAu2GeS4 (M = Co, Ni) were prepared from K2Au2GeS4 precursor and Co(OAc)2 or NiCl2 by one-pot sol-gel metathesis reactions in aqueous media. The MAu2GeS4-chalcogels were screened for catalytic intramolecular hydroamination of 4-pentyn-1-amine substrate at different temperatures. 87% and 58% conversion was achieved at 100 °C, using CoAu2GeS4- and NiAu2GeS4-chalcogels respectively, and the reaction kinetics follows the first order. It was established that the catalytic performance of the aerogels is associated with the M2+ centers present in the structure. Intermolecular hydroamination of aniline with 1-R-4-ethynylbenzene (R = -H, -OCH3, -Br, -F) was carried out at 100 °C using CoAu2GeS4-chalcogel catalyst, due to its promising catalytic performance. The CoAu2GeS4-chalcogel regioselectively converted the pair of substrates to respective Markovnikov products, (E)-1-(4-R-phenyl)-N-phenylethan-1-imine, with 38% to 60% conversion.
Perhalogenated carba-closo-dodecaborate anions as ligand substituents: Applications in gold catalysis
Lavallo, Vincent,Wright II, James H.,Tham, Fook S.,Quinlivan, Sean
supporting information, p. 3172 - 3176 (2013/04/24)
Bigger and better! The single-component zwitterionic gold catalyst formed by the coordination of a phosphine ligand bearing an inert and noncoordinating carborane substituent, CB11Cl11-, to an Au I ion exhibited
Chiral dienes as "ligands" for borane-catalyzed metal-free asymmetric hydrogenation of imines
Liu, Yongbing,Du, Haifeng
supporting information, p. 6810 - 6813 (2013/06/05)
This paper describes a highly enantioselective metal-free hydrogenation of imines using chiral dienes as "ligands" for the generation of catalysts with HB(C6F5)2 by hydroboration in situ to furnish a variety of chiral amin
Asymmetric reduction of aryl imines using Candida parapsilosis ATCC 7330
Vaijayanthi,Chadha, Anju
, p. 93 - 96 (2008/09/17)
A highly enantioselective one pot, novel biocatalytic method for the asymmetric reduction of aryl imines is reported. Treatment of aryl imines with Candida parapsilosis ATCC 7330 in aqueous medium produces the enantiomerically pure (R)-secondary amines in
Gold(III)-catalyzed double hydroamination of o-alkynylaniline with terminal alkynes leading to N-vinylindoles
Zhang, Yuhua,Donahue, James P.,Li, Chao-Jun
, p. 627 - 630 (2007/10/03)
A highly efficient double-hydroamination reaction of o-alkynylanilines with terminal alkynes leading to N-alkenylindoles was developed by using gold(III) as a catalyst under neat conditions.
Heterogeneous intermolecular hydroamination of terminal alkynes with aromatic amines
Shanbhag, Ganapati V.,Kumbar, Suresh M.,Joseph, Trissa,Halligudi, Shivappa B.
, p. 141 - 143 (2007/10/03)
Heterogeneous intermolecular hydroamination of alkynes with aromatic amines using inexpensive transition metal-exchanged clay catalysts was investigated. Reaction of terminal alkynes with aromatic amines gave higher yields of imines.
Enantioselective hydrogenation of acyclic aromatic N-aryl imines catalyzed by an iridium complex of (S,S)-1,2-bis(tert-butylmethylphosphino)ethane
Imamoto, Tsuneo,Iwadate, Noriyuki,Yoshida, Kazuhiro
, p. 2289 - 2292 (2007/10/03)
An iridium(I) complex of (S,S)-1,2-bis(tert-butylmethylphosphino)ethane with tetrakis(3,5-bis(trifluoromethyl)phenyl)borate as the counterion catalyzes the hydrogenation of acyclic aromatic N-aryl imines under 1 atm of hydrogen pressure at room temperatur
