Cited by Poly(2,2′-Bibenzimidazole)–Supported Iridium Complex: A Recyclable Metal–Polymer Ligand Bifunctional Catalyst for the <i>N</i>-Methylation of Amines with Methanol

Recent Advances for Alkylation of Ketones and Secondary Alcohols Using Alcohols in Homogeneous Catalysis DOI

Dongyuan Yang,

Hongli Wang, Chun‐Ran Chang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(18), P. 3100 - 3121

Published: July 4, 2022

Abstract The alkylation of ketones or secondary alcohols using as alkylating agents via hydrogen borrowing strategy presents a powerful method for the synthesis ɑ‐alkylated ketones. In this review, we summarize progress catalyzed by Ir, Pd, Rh, Ru, Mn, Fe, Co, Ni, and Cu catalysts α‐alkylation with cross‐coupling from 2017 to 2021. A wide range (aromatic aliphatic ketones) (benzylic primary alcohols, aromatic alkenyl diols) are well tolerated. Furthermore, also discuss current challenges propose perspectives on coming development in filed. objective present review is give an overview recent advances β‐alkylation alcohols. Finally, hope that will inspirations magnified image

Language: Английский

Citations

The α-trideuteromethylation of arylacetonitriles with deuterated methanol via deuterium autotransfer process catalyzed by a metal-ligand bifunctional iridium catalyst DOI

Deyun Liu, Xiangchao Xu, Peng Zhang

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 430, P. 115301 - 115301

Published: Jan. 18, 2024

Language: Английский

Citations

CrCl₂-catalyzed α-alkylation of carbonyl compounds via a borrowing hydrogen approach DOI

Dongyue Wei,

Baojin Feng,

Qing Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1955 - 1962

Published: Jan. 1, 2024

A new and efficient catalytic system for sustainable α-alkylation of carbonyl compounds with alcohols via a borrowing hydrogen strategy is presented.

Language: Английский

Citations

A Guide for Mono‐Selective N‐Methylation, N‐Ethylation, and N‐n‐Propylation of Primary Amines, Amides, and Sulfonamides and Their Applicability in Late‐Stage Modification DOI

Johanna Templ, Michael Schnürch

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(26)

Published: Feb. 14, 2024

Abstract This review provides a comprehensive overview of mono‐alkylation methodologies targeting crucial nitrogen moieties – amines, amides, and sulfonamides found in organic building blocks pharmaceuticals. Emphasizing the intersection chemical precision with drug discovery, central challenge addressed is achieving one‐pot mono‐selective short‐chain N‐alkylations (methylations, ethylations, n ‐propylations), preventing undesired overalkylation. Additionally, sustainable, safe, benign alternatives to traditional alkylating agents, including alcohols, carbon dioxide, carboxylic acids, nitriles, alkyl phosphates, quaternary ammonium salts, carbonates, are explored. review, categorized by nature agent, aids researchers selecting suitable methods for N‐alkylation.

Language: Английский

Citations

Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate DOI

Peng Liu, Jiazhi Yang, Yao Ai

et al.

Journal of Catalysis, Journal Year: 2021, Volume and Issue: 396, P. 281 - 290

Published: March 10, 2021

Language: Английский

Citations

Cp*Ir complex bearing a flexible bridging and functional 2,2′-methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol DOI

Xiaozhong Chen, Yao Ai, Peng Liu

et al.

Journal of Catalysis, Journal Year: 2021, Volume and Issue: 402, P. 325 - 334

Published: Aug. 26, 2021

Language: Английский

Citations

Pincer-Cobalt-Catalyzed Guerbet-Type β-Alkylation of Alcohols in Air under Microwave Conditions DOI

Pran Gobinda Nandi,

Prasad Thombare,

Siriyara Jagannatha Prathapa

et al.

Organometallics, Journal Year: 2022, Volume and Issue: 41(22), P. 3387 - 3398

Published: Aug. 5, 2022

Pincer complexes of the type (R2NNN)CoCl2 (R = iPr, tBu, Cy, Ph, p-F-C6H4) derived from environmentally benign, earth-abundant, and inexpensive base metal cobalt have been synthesized that exist in equilibrium with [(R2NNN)2Co]CoCl4. Among these complexes, (iPr2NNN)CoCl2 has found to be highly efficient for catalytic β-alkylation alcohols air at 140 °C. While pincer-Co (0.0025 mol %)-catalyzed presence NaOtBu (2.5 %) took 24 h (85%, 34000 TON 1417 TO/h) under conventional heating (140 °C), corresponding reaction microwave conditions °C 75 W) was complete only 2 comparable yields (83%, 33200 TON), albeit a better TOF (16600 TO/h). In contrast, CoCl2 otherwise identical leads lower both (66%, 26400 1100 (61%, 24400 12200 The system successfully implemented (39 examples) accomplish secondary several primary alcohols. Well-defined molecular Co(II) species are involved during catalysis, as inferred HRMS hot-filtration experiments. EPR studies magnetic moment measurements using Evans method demonstrate Co remains its +2 state an octahedral geometry throughout reaction. Pivotal evidence involvement β-hydride elimination leading acetophenone RDS catalyzed is obtained competitive deuterium labeling experiments, which indicative KIE 6.14. current report on base-metal catalysis high unprecedented turnovers (33200 16600 very short time (2 h) offers exciting atom-economical greener possibilities class synthetically valuable Guerbet-type reactions.

Language: Английский

Citations

Recent Development in Synthesis of N‐Methylamines with Amines and Methanol DOI

Xiaogang Yu, Xinjiang Cui, Huanwang Jing

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(16)

Published: March 23, 2024

Abstract The N‐methylation reaction of amines with methanol via the borrowing‐hydrogen strategy is an important method for construction C−N bonds. Compared other C1 sources, such as toxic formaldehyde or expensive formic acid, more suitable reactions due to its eco‐friendliness and low price. Using this strategy, various types N‐methylated products, including biological pharmaceutical molecules have been prepared. Here, we present a thorough survey decades articles showing current developments in methanol. We discuss homogenous, heterogenous light‐driven catalytic systems both N,N‐dimethylation reactions. This review presents shortcomings provides future development progress

Language: Английский

Citations

A Catalyst‐Free Minisci‐Type Reaction: the C–H Alkylation of Quinoxalinones with Sodium Alkylsulfinates and Phenyliodine(III) Dicarboxylates DOI

Liping Wang, Jiquan Zhao,

Yuting Sun

et al.

European Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 2019(41), P. 6935 - 6944

Published: Oct. 7, 2019

A direct C–H alkylation of quinoxalinones at the C‐3 position with sodium alkylsulfinates and phenyliodine(III) dicarboxylates has been developed under catalyst‐free conditions. series 3‐alkylquinoxalinones were afforded in moderate to excellent yields this protocol, which offers a practical efficient access biologically interesting 3‐alkylquinoxalin‐2(1 H )‐one derivatives.

Language: Английский

Citations

Peroxide-mediated site-specific C–H methylation of imidazo[1,2-a]pyridines and quinoxalin-2(1H)-ones under metal-free conditions DOI

Shengzhou Jin,

Hua Yao,

Sen Lin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 18(2), P. 205 - 210

Published: Nov. 28, 2019

An effective approach to realize the direct methylation of imidazo[1,2-a]pyridines and quinoxalin-2(1H)-ones with peroxides under metal-free conditions is described. In this protocol, serve as both radical initiator methyl source. Methylated imidazopyridines were smoothly synthesized in moderate good yields. A free reaction mechanism was proposed describe process.

Language: Английский

Citations