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

[41] Scandium(III)-Catalyzed N-Alkylation of Carbazoles with Alcohols [J].

Niu, Yu-Dan ;

Lv, Pei ;

Hu, Hao-Lan ;

Shi, Jianghuan ;

Chen, Peng ;

Jiang, Yi-Jun .

Synthesis (Germany), 2025, 57 (06) :1223-1229

[42] N-alkylation of ammonia and amines with alcohols catalyzed by Ni-loaded CaSiO3 [J].

Shimizu, Ken-ichi ;

Kanno, Shota ;

Kon, Kenichi ;

Siddiki, S. M. A. Hakim ;

Tanaka, Hideyuki ;

Sakata, Yoshihisa .

CATALYSIS TODAY, 2014, 232 :134-138

[43] N-Alkylation and N,C-Dialkylation of Amines with Alcohols in the Presence of Ruthenium Catalysts with Chelating N-Heterocyclic Carbene Ligands [J].

Sahin, Zeynel ;

Gurbuz, Nevin ;

Ozdemir, Ismail ;

Sahin, Onur ;

Buyukgungor, Orhan ;

Achard, Mathieu ;

Bruneau, Christian .

ORGANOMETALLICS, 2015, 34 (11) :2296-2304

[44] Boron-Catalyzed N-Alkylation of Arylamines and Arylamides with Benzylic Alcohols [J].

Guru, Murali Mohan ;

Thorve, Pradip Ramdas ;

Maji, Biplab .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02) :806-819

[45] Silver nanoparticles supported over mesoporous alumina as an efficient nanocatalyst for N-alkylation of hetero (aromatic) amines and aromatic amines using alcohols as alkylating agent [J].

Paul, Priyanka ;

Bhanja, Piyali ;

Salam, Noor ;

Mandi, Usha ;

Bhaumik, Asim ;

Alam, Seikh Mafiz ;

Islam, Sk. Manirul .

JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2017, 493 :206-217

[46] Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols [J].

Feng, Xinshu ;

Huang, Ming .

POLYHEDRON, 2021, 205

[47] Scalable synthesis of secondary and tertiary amines by heterogeneous Pt-Sn/γ-Al2O3 catalyzed N-alkylation of amines with alcohols [J].

Wu, Kaikai ;

He, Wei ;

Sun, Chenglin ;

Yu, Zhengkun .

TETRAHEDRON, 2016, 72 (51) :8516-8521

[48] Ni-Cu/γ-Al2O3 catalyzed N-alkylation of amines with alcohols [J].

Sun, Jian ;

Jin, Xiaodong ;

Zhang, Fengwei ;

Hu, Wuquan ;

Liu, Juntao ;

Li, Rong .

CATALYSIS COMMUNICATIONS, 2012, 24 :30-33

[49] Tungsten-Catalyzed Direct N-Alkylation of Anilines with Alcohols [J].

Lan, Xiao-Bing ;

Ye, Zongren ;

Yang, Chenhui ;

Li, Weikang ;

Liu, Jiahao ;

Huang, Ming ;

Liu, Yan ;

Ke, Zhuofeng .

CHEMSUSCHEM, 2021, 14 (03) :860-865

[50] Fe(II)-catalyzed N-alkylation of sulfonamides with benzylic alcohols [J].

Cui, Xinjiang ;

Shi, Feng ;

Zhang, Yan ;

Deng, Youquan .

TETRAHEDRON LETTERS, 2010, 51 (15) :2048-2051

← 1 2 3 4 5 →