An Efficient Palladium-Catalyzed N-Alkylation of Amines Using Primary and Secondary Alcohols

被引：140

作者：

Tuan Thanh Dang ^{[1
]}

Ramalingam, Balamurugan ^{[1
]}

Shan, Siah Pei ^{[1
]}

Seayad, Abdul Majeed ^{[1
]}

机构：

[1] Inst Chem & Engn Sci, Singapore 138665, Singapore

来源：

ACS CATALYSIS | 2013年 / 3卷 / 11期

关键词：

alkylation; alcohol activation; hydrogen borrowing; palladium catalyst; amine synthesis; ASTERISK-IR COMPLEX; TRANSFER HYDROGENATION; COUPLING REACTIONS; DEHYDRATIVE ALKYLATION; SELECTIVE ALKYLATION; HETEROCYCLIC CARBENE; RECYCLABLE CATALYST; REDUCTIVE AMINATION; HIGHLY EFFICIENT; IRIDIUM COMPLEX;

D O I：

10.1021/cs400799n

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

PdCl2 in the presence of dppe or Xantphos(t-Bu) as the ligand is found to be an efficient catalyst for the N-alkylation of various primary and cyclic secondary amines using primary alcohols at 90-130 degrees C under neat conditions. Interestingly, good to excellent yields were achieved when more challenging secondary alcohols were used as alkylating agents at 130-150 degrees C. The reaction could be easily scaled up, as demonstrated for a 10 mmol scale achieving yields up to 90% with a TON of 900.

引用

收藏

页码：2536 / 2540

页数：5

相关论文

共 50 条

[21] Heterogeneous catalyzed N-alkylation of amines with alcohols via borrowing hydrogen methodology [J].

Zou, Yiwen ;

Ma, Zhuang ;

Dong, Lin ;

Yang, Yong ;

Wang, Ping ;

Sheng, Shixiong ;

Zboril, Radek ;

Jagadeesh, Rajenahally, V ;

Chen, Zupeng .

COORDINATION CHEMISTRY REVIEWS, 2025, 541

[22] Efficient and Clean Gold-Catalyzed One-Pot Selective N-Alkylation of Amines with Alcohols [J].

He, Lin ;

Lou, Xia-Bing ;

Ni, Ji ;

Liu, Yong-Mei ;

Cao, Yong ;

He, He-Yong ;

Fan, Kang-Nian .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (47) :13965-13969

[23] Ruthenium Complexes Bearing α-Diimine Ligands and Their Catalytic Applications in N-Alkylation of Amines, α-Alkylation of Ketones, and β-Alkylation of Secondary Alcohols [J].

Gayathri, Sekar ;

Viswanathamurthi, Periasamy ;

Bertani, Roberta ;

Sgarbossa, Paolo .

ACS OMEGA, 2022, :33107-33122

[24] Use of a Cyclometalated Iridium(III) Complex Containing a N∧C∧N-Coordinating Terdentate Ligand as a Catalyst for the α-Alkylation of Ketones and N-Alkylation of Amines with Alcohols [J].

Liu, Pengcheng ;

Lang, Ran ;

Lu, Lei ;

Yu, Zhentao ;

Li, Feng .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (04) :1943-1950

[25] Insight into O2-Promoted Base-Catalyzed N-Alkylation of Amines with Alcohols [J].

Wang, Chao ;

Chen, Changpeng ;

Han, Jian ;

Zhang, Jingyu ;

Yao, Yingming ;

Zhao, Yingsheng .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (13) :2972-2977

[26] General Synthesis of N-Alkylation of Amines with Secondary Alcohols via Hydrogen Autotransfer [J].

Subaramanian, Murugan ;

Midya, Siba P. ;

Ramar, Palmurukan M. ;

Balaraman, Ekambaram .

ORGANIC LETTERS, 2019, 21 (22) :8899-8903

[27] Tris(acetylacetonato)rhodium(III)-Catalyzed α-Alkylation of Ketones, β-Alkylation of Secondary Alcohols and Alkylation of Amines with Primary Alcohols [J].

Satyanarayana, Ponnam ;

Reddy, Ganapam Manohar ;

Maheswaran, Hariharasharma ;

Kantam, Mannepalli Lakshmi .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) :1859-1867

[28] Efficient ruthenium(II) complex catalyzed N-alkylation of amines and ?-alkylation of secondary alcohol via borrowing hydrogen methodology [J].

Vijayapritha, Subbarayan ;

Nithya, Paramasivan ;

Viswanathamurthi, Periasamy ;

Raju, Saravanan ;

Linert, Wolfgang .

POLYHEDRON, 2023, 235

[29] Pd/C as an Efficient and Reusable Catalyst for the Selective N-Alkylation of Amines with Alcohols [J].

Liu, Xiang ;

Hermange, Philippe ;

Ruiz, Jaime ;

Astruc, Didier .

CHEMCATCHEM, 2016, 8 (06) :1043-1045

[30] Inorganic Iodide Catalyzed Alkylation of Amines with Primary Alcohols [J].

Geng, Shihan ;

Jiang, Changwei ;

Li, Zhaoting ;

Wang, Hongye ;

Gao, Yihan ;

Wang, Zirun ;

Liu, Qiang ;

Jiao, Ning ;

Song, Song .

CCS CHEMISTRY, 2025,

← 1 2 3 4 5 →