Series on chemistry, energy and the environment, Journal Year: 2022, Volume and Issue: unknown, P. 281 - 367
Published: June 22, 2022
(II)
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(12), P. 3216 - 3220
Published: Feb. 14, 2017
Abstract Herein, a general and efficient method for the homogeneous cobalt‐catalyzed hydrogenation of N‐heterocycles, under mild reaction conditions, is reported. Key to success use tetradentate ligand tris(2‐(diphenylphosphino)phenyl)phosphine). This non‐noble metal catalyst system allows selective heteroarenes in presence broad range other sensitive reducible groups.
Language: Английский
Citations
160
Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(10), P. 5108 - 5113
Published: Nov. 26, 2020
Abstract The non‐noble metal‐catalyzed asymmetric hydrogenation of N‐heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the affording high yields and enantioselectivities (up to 97 % ee). turnover number 3840 was reached at a low loading (S/C=4000), which competitive with most effective noble metal catalysts for this reaction. precise regulation enantioselectivity were ensured by π–π interaction.
Language: Английский
Citations
132
Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(14), P. 4664 - 4668
Published: Feb. 14, 2019
A new series of spiro-bicyclic bisborane catalysts has been prepared by means hydroboration reactions C2 -symmetric dienes with HB(C6 F5 )2 and HB(p-C6 F4 H)2 . When used for hydrogenation quinolines, these give excellent yields enantiomeric excesses, show turnover numbers up to 460. The most attractive feature metal-free was the broad functional-group tolerance, making this method complementary existing methods quinoline hydrogenation.
Language: Английский
Citations
78
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(20)
Published: March 3, 2022
The asymmetric hydrogenation (AH) of 3H-indoles represents an ideal approach to the synthesis useful chiral indoline scaffolds. However, very few catalytic systems based on precious metals have been developed realize this challenging reaction. Herein, we report a Mn-catalyzed AH with excellent yields and enantioselectivities. kinetic resolution racemic by was also achieved high s-factors construct quaternary stereocenters. Many acid-sensitive functional groups, which cannot be tolerated when using state-of-the-art ruthenium catalyst, were compatible manganese catalysis. This new process expands scope transformation highlights uniqueness earth-abundant metal reaction could proceed catalyst loadings at parts per million (ppm) level exceptional turnover number 72 350. is highest value yet reported for metal-catalyzed
Language: Английский
Citations
55
Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(15), P. 4135 - 4139
Published: March 15, 2017
Abstract The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting Cu(OTf) 2 and chiral cationic ruthenium–diamine complex. A range 1 H ‐isochromenes were obtained high yields good to excellent enantioselectivity. These could be easily transformed into isochromanes, which represent an important structural motif natural products biologically active compounds. induction was rationalized density functional theory calculations.
Language: Английский
Citations
60
Angewandte Chemie, Journal Year: 2017, Volume and Issue: 129(12), P. 3264 - 3268
Published: Feb. 14, 2017
Abstract Herein, a general and efficient method for the homogeneous cobalt‐catalyzed hydrogenation of N‐heterocycles, under mild reaction conditions, is reported. Key to success use tetradentate ligand tris(2‐(diphenylphosphino)phenyl)phosphine). This non‐noble metal catalyst system allows selective heteroarenes in presence broad range other sensitive reducible groups.
Language: Английский
Citations
55
Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(47), P. 16831 - 16834
Published: Sept. 5, 2019
A highly enantioselective iridium- or ruthenium-catalyzed intermolecular reductive amination/asymmetric hydrogenation relay with 2-quinoline aldehydes and aromatic amines has been developed. broad range of sterically tunable chiral N,N'-diaryl vicinal diamines were obtained in high yields (up to 95 %) excellent enantioselectivity >99 % ee). The resulting could be readily transformed into hindered N-heterocyclic carbene (NHC) precursors, which are otherwise difficult access. usefulness this synthetic approach was further demonstrated by the successful application one NHC ligands a transition-metal-catalyzed asymmetric Suzuki-Miyaura cross-coupling reaction ring-opening cross-metathesis, respectively.
Language: Английский
Citations
46
Angewandte Chemie, Journal Year: 2017, Volume and Issue: 129(15), P. 4199 - 4203
Published: March 15, 2017
Abstract The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting Cu(OTf) 2 and chiral cationic ruthenium–diamine complex. A range 1 H ‐isochromenes were obtained high yields good to excellent enantioselectivity. These could be easily transformed into isochromanes, which represent an important structural motif natural products biologically active compounds. induction was rationalized density functional theory calculations.
Language: Английский
Citations
26
Angewandte Chemie, Journal Year: 2020, Volume and Issue: 133(10), P. 5168 - 5173
Published: Nov. 26, 2020
Abstract The non‐noble metal‐catalyzed asymmetric hydrogenation of N‐heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the affording high yields and enantioselectivities (up to 97 % ee). turnover number 3840 was reached at a low loading (S/C=4000), which competitive with most effective noble metal catalysts for this reaction. precise regulation enantioselectivity were ensured by π–π interaction.
Language: Английский
Citations
23
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(4), P. 2282 - 2293
Published: Jan. 19, 2023
The palladium complex [(L1)Pd(μ-OAc)]2[OTf]2 (L1 = neocuproine) is a selective catalyst for the aerobic oxidation of vicinal polyols to α-hydroxyketones, but competitive ligand methyl groups limits turnover number and necessitates high Pd loadings. Replacement neocuproine with 2,2'-biquinoline ligands was investigated as strategy improve performance explore relationship between structure reactivity. Evaluation [(L2)Pd(μ-OAc)]2[OTf]2 (L2 2,2'-biquinoline) alcohol revealed threefold enhancement in relative congener, much slower rate. Mechanistic studies indicated that slow rates observed L2 were consequence precipitation an insoluble trinuclear species─(L2Pd)3(μ-O)22+─formed during catalysis characterized by high-resolution electrospray ionization mass spectrometry. Density functional theory used predict sterically modified biquinoline ligand, L3 7,7'-di-tert-butyl-2,2'-biquinoline, would disfavor formation (LPd)3(μ-O)22+ species. This design validated catalytic [(L3)Pd(μ-OAc)]2[OTf]2 both robust rapid, marrying kinetics parent L1-supported system numbers L2-supported system. Changes also found modulate regioselectivity glycoside substrates, providing new insights into structure-selectivity relationships this class catalysts.
Language: Английский
Citations
7