Phosphine‐Functionalized Syndiotactic Polystyrenes: Synthesis and Application to Immobilization of Transition Metal Nanoparticle Catalysts DOI
Lei Jiang,

Yinran Wang,

Hanyang Sun

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 28(62)

Published: July 12, 2022

The precise control of monomer sequence and stereochemistry in copolymerization is much interest importance for the synthesis high performance materials, but studies toward this goal have met with only limited success to date. coordination polymerization diphenylphosphinostyrene (p-StPPh2 o-StPPh2 ) its styrene (St) by (C5 Me4 SiMe3 )Sc(CH2 C6 H4 NMe2 -o)2 been achieved first time afford a new series phosphine functionalized syndiotactic polystyrene. By design polymer structure, copolymer St (poly(o-StPPh2 -alt-St)-b-sPS) containing atactic alternating block polystyrene (sPS) showed excellent thermal stability chemical resistance. simple combination triphenylphosphine realized stable immobilization metal nanoparticles highly robust metal@poly(o-StPPh2 -alt-St)-b-sPS nanocatalysts at temperature various atmospheres. Cu@poly(o-StPPh2 catalyst can serve as efficient heterogeneous quinoline derivatives acceptorless dehydrogenative coupling o-aminobenzylalcohol ketones.

Language: Английский

Multi-Functionality of Methanol in Sustainable Catalysis: Beyond Methanol Economy DOI
Ganesan Sivakumar, Rohit Kumar, Vinita Yadav

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(22), P. 15013 - 15053

Published: Nov. 6, 2023

Methanol is a fundamental feedstock and widely used in the chemical petroleum industries. It can serve as C1 source to make variety of C–C C–N bond formation dehydrogenative coupling products, which have important applications natural products drug discovery. A high hydrogen content (12.5 wt%) methanol makes it an effective H2 donor for transfer hydrogenation various reducible functional groups. plethora transition metal-based processes been developed using methanol. Notably, recent review articles focused on aspect However, more updated that examines challenges both C1-source H2-source organic transformations contributing concept economy has not presented yet. This Review summarizes (homogeneous, heterogeneous, photo-) catalyst system C-, N-, O-methylation ketones, alcohols, amides, nitriles, heterocyclic compounds, sulfones, amines, sulfonamides direct N-methylation nitro compounds under borrowing strategy N-formylation amines acceptorless dehydrogenation source. also covers insights into reaction mechanisms role carefully selected ligands metal catalysis activation incorporation -CD3, methylation molecules. Moreover, describes groups such aldehydes, alkynes, with detail.

Language: Английский

Citations

31

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

10

Recent advances in sustainable organic transformations using methanol: expanding the scope of hydrogen-borrowing catalysis DOI
Lalit Mohan Kabadwal, Sourajit Bera, Debasis Banerjee

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(24), P. 7077 - 7096

Published: Jan. 1, 2021

Recent progress relating to sustainable approaches using methanol as a C1-alkylating agent for C–Me and N–Me bond formation is discussed.

Language: Английский

Citations

49

Recent advances in the catalytic N-methylation and N-trideuteromethylation reactions using methanol and deuterated methanol DOI
Vishakha Goyal, Naina Sarki, N. ANAND

et al.

Coordination Chemistry Reviews, Journal Year: 2022, Volume and Issue: 474, P. 214827 - 214827

Published: Oct. 11, 2022

Language: Английский

Citations

34

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 Creative Commons
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

7

Tunable mono- and di-methylation of amines with methanol over bimetallic CuCo nanoparticle catalysts DOI
Keming Li, Qi Zhang,

Zhong-Ming Xu

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(15), P. 5965 - 5977

Published: Jan. 1, 2022

Heterogeneous non-noble bimetallic CuCo nanoparticle catalysts for selective N -monomethylation and , -dimethylation reactions under base-free conditions, offering >50 examples from aromatic/aliphatic amines, nitrocompounds different alcohols.

Language: Английский

Citations

12

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, Journal Year: 2024, Volume and Issue: 136(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

2

A bimetallic PdCu–Fe3O4catalyst with an optimal d-band centre for selectiveN-methylation of aromatic amines with methanol DOI
Jin Hee Cho, Yoonhoo Ha, Ahra Cho

et al.

Catalysis Science & Technology, Journal Year: 2022, Volume and Issue: 12(11), P. 3524 - 3533

Published: Jan. 1, 2022

Highly efficient and selective N -methylation of aniline with methanol is possible Pd 1 Cu 0.6 –Fe 3 O 4 nanoparticle catalyst.

Language: Английский

Citations

8

Catalysis‐Controlled Selective N‐mono or N‐di‐methylation of Anilines: A Review on Synthesis of N‐methyl or N,N‐dimethyl anilines DOI
Fuhua Zhang,

Kun Chen,

Xin Min

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(3)

Published: Jan. 16, 2024

Abstract N ‐alkyl anilines are a series of common and versatile compounds which not only have been used as reaction solvents, acid‐accepters, organic‐bases, but also in synthesis dyes, pharmaceuticals, anti‐colodal. The ‐methyl and/or , ‐dimethyl the most representative ones among these. Due to their widespread uses, numerous works reported on synthetic strategies past decades. studies N−H methylations mainly focus selection reagents, catalysts, or ligands design. Different transition‐metals, e. g., Ir, Ru, Pd, et. al, with different methylation protocols. Methanol (CH 3 OH), carbon dioxide (CO 2 ), formaldehyde (HCHO), dimethyl carbonate ((CH ) CO was C source, hydrogen (H silanes H source. In this work, we would like summarize latest advances ( included) derivatives. This review provides an overview reactants catalyst, well emphasis scope substrates proposed mechanism for each work.

Language: Английский

Citations

1

Synthesis of N- and C-terpenylanilines and the study of their properties DOI
I. Yu. Chukicheva, O. A. Shumova, О. Г. Шевченко

et al.

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(3), P. 580 - 587

Published: March 1, 2024

Language: Английский

Citations

1