864832-24-6Relevant articles and documents
Olefin Hydroarylation Catalyzed by a Single-Component Cobalt(-I) Complex
Suslick, Benjamin A.,Tilley, T. Don
supporting information, p. 1495 - 1499 (2021/03/03)
A single-component Co(-I) catalyst, [(PPh3)3Co(N2)]Li(THF)3, has been developed for olefin hydroarylations with (N-aryl)aryl imine substrates. More than 40 examples were examined under mild reaction conditions to afford the desired alkyl-arene product in good to excellent yields. Catalysis occurs in a regioselective manner to afford exclusively branched products with styrene-derived substrates or linear products for aliphatic olefins. Electron-withdrawing functional groups (e.g., -F, -CF3, and -CO2Me) were tolerated under the reaction conditions.
A Multicatalytic Approach to the Hydroaminomethylation of α-Olefins
Hanna, Steven,Holder, Jeffrey C.,Hartwig, John F.
supporting information, p. 3368 - 3372 (2019/02/24)
We report an approach to conducting the hydroaminomethylation of diverse α-olefins with a wide range of alkyl, aryl, and heteroarylamines at relatively low temperatures (70–80 °C) and pressures (1.0–3.4 bar) of synthesis gas. This approach is based on sim
Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
supporting information, p. 647 - 654 (2018/10/24)
Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
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.
, 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
C-H activation/functionalization catalyzed by simple, well-defined low-valent cobalt complexes
Fallon, Brendan J.,Derat, Etienne,Amatore, Muriel,Aubert, Corinne,Chemla, Fabrice,Ferreira, Franck,Perez-Luna, Alejandro,Petit, Marc
supporting information, p. 2448 - 2451 (2015/03/04)
A facile C-H activation and functionalization of aromatic imines is presented using low-valent cobalt catalysts. Using Co(PMe3)4 as catalyst we have developed an efficient and simple protocol for the C-H/hydroarylation of alkynes wit
Palladium-catalyzed condensation of N -aryl imines and alkynylbenziodoxolones to form multisubstituted furans
Lu, Beili,Wu, Junliang,Yoshikai, Naohiko
supporting information, p. 11598 - 11601 (2014/10/16)
A palladium(II) catalyst promotes condensation of an N-aryl imine and an alkynylbenziodoxolone derivative to afford a multisubstituted furan, whose substituents are derived from the alkynyl moiety (2-position), the imine (3- and 4-positions), and the 2-iodobenzoate moiety (5-position), along with an N-arylformamide under mild conditions. The 2-iodophenyl group of the furan product serves as a versatile handle for further transformations. A series of isotope-labeling experiments shed light on the bond reorganization process in this unusual condensation reaction, which includes cleavage of the C-C triple bond and fragmentation of the carboxylate moiety.
Asymmetric hydrogenation of N-alkyl and N-aryl ketimines using chiral cationic Ru(diamine) complexes as catalysts: The counteranion and solvent effects, and substrate scope
Chen, Fei,Ding, Ziyuan,He, Yanmei,Qin, Jie,Wang, Tianli,Fan, Qing-Hua
supporting information; experimental part, p. 5248 - 5257 (2012/08/08)
Asymmetric hydrogenation of N-alkyl and N-aryl ketimines catalyzed by chiral cationic η6-arene-(N-monosulfonylated diamine) Ru(II) complexes has been investigated. Strong counteranion and solvent effects on the enantioselectivity were observed. The ruthenium catalyst bearing non-coordinating BArF- anion was found to be particularly effective for the hydrogenation of acyclic and exocyclic N-alkyl ketimines in the presence of (Boc)2O in dichloromethane or even under solvent-free conditions, providing chiral amines with up to >99% ee and full conversions. Alternatively, the ruthenium catalyst bearing achiral phosphate anion together with corresponding phosphoric acid as the additive was also efficient for the hydrogenation of N-alkyl ketimines in the absence of (Boc)2O with excellent enantioselectivities and full conversions. For N-aryl ketimines lower enantiomeric excesses were observed by using the ruthenium catalyst bearing BArF- anion. This catalytic protocol thus provides a facile and practical access to optically active amines and has been successfully employed in the gram-scale synthesis of enantiomerically pure (+)-sertraline.
Asymmetric reduction of ketimines with trichlorosilane employing an imidazole derived organocatalyst
Gautier, Franois-Moana,Jones, Simon,Martin, Stephen J.
supporting information; experimental part, p. 229 - 231 (2009/03/11)
Organocatalysts for the asymmetric reduction of ketimines are presented that function well at low catalyst loadings providing chiral amines in good yield and enantioselectivity, the latter appearing to be independent of the ketimine substrate geometry.
S-chiral sulfinamides as highly enantioselective organocatalysts
Pei, Dong,Wang, Zhouyu,Wei, Siyu,Zhang, Yu,Sun, Jian
, p. 5913 - 5915 (2007/10/03)
(Diagram presented) Easily accessible chiral sulfinamide 2 has been developed as the first highly efficient and enantioselective organocatalyst relying solely on a chiral sulfur center for stereochemical induction. In the presence of 20 mol % of 2, a broa
