Reusable Co-nanoparticles for general and selective N-alkylation of amines and ammonia with alcohols DOI Creative Commons
Zhuang Ma, Bei Zhou, Xinmin Li

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 13(1), P. 111 - 117

Published: Nov. 29, 2021

A general cobalt-catalyzed

Metal-Catalyzed Enantioconvergent Transformations DOI Creative Commons
Miguel Yus, Carmén Nájera, Francisco Foubelo

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(20), P. 11817 - 11893

Published: Oct. 4, 2023

Enantioconvergent catalysis has expanded asymmetric synthesis to new methodologies able convert racemic compounds into a single enantiomer. This review covers recent advances in transition-metal-catalyzed transformations, such as radical-based cross-coupling of alkyl electrophiles with nucleophiles or alkylmetals and reductive two mainly under Ni/bis(oxazoline) catalysis. C–H functionalization can be performed an enantioconvergent manner. Hydroalkylation alkenes, allenes, acetylenes is alternative reactions. Hydrogen autotransfer been applied amination alcohols C–C bond forming reactions (Guerbet reaction). Other metal-catalyzed involve addition allylic systems carbonyl compounds, propargylation phenols, 3-bromooxindoles, allenylation allenolates propargyl bromides, hydroxylation 1,3-dicarbonyl compounds.

Language: Английский

Citations

37
Transition metal-catalysis in interrupted borrowing hydrogen strategy DOI Creative Commons
Madhu Nallagangula, Murugan Subaramanian, Rohit Kumar

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(51), P. 7847 - 7862

Published: Jan. 1, 2023

This review article highlights the recent advances of transition-metal-catalyzed interrupted borrowing hydrogen (IBH) catalysis and its applications in sustainable affordable chemical synthesis using alcohols as C1 feedstocks.

Language: Английский

Citations

34
Iridium-Catalyzed Enantioconvergent Borrowing Hydrogen Annulation of Racemic 1,4-Diols with Amines DOI
Yongbing Liu,

Huanlin Diao,

Guorong Hong

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(9), P. 5007 - 5016

Published: Feb. 21, 2023

We present an enantioconvergent access to chiral N-heterocycles directly from simple racemic diols and primary amines, through a highly economical borrowing hydrogen annulation. The identification of amine-derived iridacycle catalyst was the key for achieving high efficiency enantioselectivity in one-step construction two C-N bonds. This catalytic method enabled rapid wide range diversely substituted enantioenriched pyrrolidines including precursors valuable drugs such as aticaprant MSC 2530818.

Language: Английский

Citations

33
Divergent Synthesis of Alcohols and Ketones via Cross‐Coupling of Secondary Alcohols under Manganese Catalysis DOI

Feixiang Sun,

Jiamin Huang,

Zhihong Wei

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(26)

Published: April 21, 2023

A homogeneous manganese-catalyzed cross-coupling of two secondary alcohols for the divergent synthesis γ-disubstituted and β-disubstituted ketones is reported. Employing well-defined Mn-MACHOPh as catalyst, this novel protocol has a broad substrate scope with good functional group tolerance affords diverse library valuable disubstituted in moderate to yields. The strong influence reaction temperature on selective formation alcohol products was theorized preliminary DFT studies. Studies have shown that Gibbs free energy thermodynamically more favourable than corresponding at lower temperature.

Language: Английский

Citations

31
Pyrazolyl-pyrimidine porous-organic-polymer supported single-site nickel composites as efficient catalysts for the synthesis of substituted pyrimidines DOI
Jiahao Li, Wei Zeng, Likui Wang

et al.

Chemical Engineering Journal, Journal Year: 2023, Volume and Issue: 474, P. 145642 - 145642

Published: Aug. 25, 2023

Language: Английский

Citations

27
Copper/Ruthenium Relay Catalysis for Stereodivergent Access to δ‐Hydroxy α‐Amino Acids and Small Peptides DOI
Cong Fu, Ling He, Xin Chang

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(7)

Published: Dec. 29, 2023

Abstract An atom‐ and step‐economical redox‐neutral cascade reaction enabled by asymmetric bimetallic relay catalysis merging a ruthenium‐catalyzed borrowing‐hydrogen with copper‐catalyzed Michael addition has been realized. A variety of highly functionalized 2‐amino‐5‐hydroxyvaleric acid esters or peptides bearing 1,4‐non‐adjacent stereogenic centers have prepared in high yields excellent enantio‐ diastereoselectivity. Judicious selection rational modification the Ru catalysts careful tuning conditions played pivotal role stereoselectivity control as well attenuating undesired α‐epimerization, thus enabling full complement all four stereoisomers that were otherwise inaccessible previous work. Concise stereodivergent synthesis key intermediates for biologically important chiral molecules further showcases synthetic utility this methodology.

Language: Английский

Citations

24
Recent advances on cross-coupling of alcohols via borrowing hydrogen catalysis DOI

Suteerna Mullick,

Adrija Ghosh, Debasis Banerjee

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(30), P. 4002 - 4014

Published: Jan. 1, 2024

This article highlights the recent advances and significance of β-alkylation reactions towards synthesis higher order alcohols.

Language: Английский

Citations

14
Single-Atom Fe-Catalyzed Acceptorless Dehydrogenative Coupling to Quinolines DOI

Yanze Lu,

Zhu Meiling,

Sanxia Chen

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(33), P. 23338 - 23347

Published: Aug. 6, 2024

A single-atom iron catalyst was found to exhibit exceptional reactivity in acceptorless dehydrogenative coupling for quinoline synthesis, outperforming known homogeneous and nanocatalyst systems. Detailed characterizations, including aberration-corrected HAADF-STEM, XANES, EXAFS, jointly confirmed the presence of atomically dispersed centers. Various functionalized quinolines were efficiently synthesized from different amino alcohols a range ketones or alcohols. The achieved turnover number (TON) up 10

Language: Английский

Citations

10
Air-Stable Coordinatively Unsaturated Ruthenium(II) Complex for Ligand Binding and Catalytic Transfer Hydrogenation of Ketones from Ethanol DOI
Alicia Beaufils,

Philipp Melle,

Nicolas Lentz

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(4), P. 2072 - 2081

Published: Jan. 17, 2024

Coordinatively unsaturated complexes are interesting from a fundamental level for their formally empty coordination site and, in particular, catalytic perspective as they provide opportunities substrate binding and transformation. Here, we describe the synthesis of novel underligated ruthenium complex [Ru(cym)(N,N')]

Language: Английский

Citations

9
Manganese‐Catalyzed Mono‐N‐Methylation of Aliphatic Primary Amines without the Requirement of External High‐Hydrogen Pressure DOI

Jiale Ji,

Yinghao Huo,

Zhaowen Dai

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(13)

Published: Feb. 1, 2024

Abstract The synthesis of mono‐ N ‐methylated aliphatic primary amines has traditionally been challenging, requiring noble metal catalysts and high‐pressure H 2 for achieving satisfactory yields selectivity. Herein, we developed an approach the selective coupling methanol amines, without hydrogen, using a manganese‐based catalyst. Remarkably, up to 98 % with broad substrate scope were achieved at low catalyst loadings. Notably, due weak base‐catalyzed alcoholysis formamide intermediates, our novel protocol not only obviates addition but also prevents side secondary ‐methylation, supported by control experiments density functional theory calculations.

Language: Английский

Citations

8