Ligand effect of cyclometallated iridium(III) complexes on N-alkylation of amines in hydrogen borrowing reactions

被引:2
|
作者
Chen, Yi-Sheng [1 ]
Chiu, Siang-Yu [1 ]
Li, Chia-Ying [1 ]
Chen, Tsun-Ren [1 ]
Chen, Jhy-Der [2 ]
机构
[1] Natl Ping Tung Univ, Dept Appl Chem, Pingtong City, Taiwan
[2] Chung Yuan Christian Univ, Dept Chem, Chungli, Taiwan
关键词
CATALYZED ALKYLATION; DERIVATIVES; ALCOHOLS; ANCILLARY; EFFICIENT; SECONDARY; HALIDES; BASE;
D O I
10.1039/d3ra07184g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dinuclear iridium complexes with the general formula (C boolean AND N)(2)Ir(mu-Cl)(2)Ir(C boolean AND N)(2) (C boolean AND N = bidentate ligand with carbon and nitrogen donor atoms) were prepared and used in catalytic systems for N-alkylation of amines through the hydrogen borrowing pathway. Triphenylphosphine derivatives were used as auxiliary in catalytic systems to provide excellent conversion of amines to N-alkylation products in yields ranging from 57% to 100%. The catalytic ability of the catalyst depends on the structure of its coordination ligands, including bidentate ligands (C boolean AND N) and triphenylphosphine derivatives. These catalytic systems adopt an environmentally friendly and sustainable reaction process through a hydrogen self-transfer strategy, using readily available alcohols as alkylating agents without the need for bases, solvents, and other additives, showing potential in the synthetic and pharmaceutical industries.
引用
收藏
页码:31948 / 31961
页数:14
相关论文
共 50 条
  • [1] Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols
    Feng, Xinshu
    Huang, Ming
    POLYHEDRON, 2021, 205
  • [2] Cyclometalated Iridium Complex-Catalyzed N-Alkylation of Amines with Alcohols via Borrowing Hydrogen in Aqueous Media
    Luo, NianHua
    Zhong, YuHong
    Wen, HuiLing
    Luo, Renshi
    ACS OMEGA, 2020, 5 (42): : 27723 - 27732
  • [3] Organometallic iridium dithiolato complexes catalyzed N-alkylation of amines with alcohols
    Xu, Chang
    Goh, Lai Yoong
    Pullarkat, Sumod A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [4] N-Alkylation of amines through hydrogen borrowing over a heterogeneous Cu catalyst
    Santoro, Federica
    Psaro, Rinaldo
    Ravasio, Nicoletta
    Zaccheria, Federica
    RSC ADVANCES, 2014, 4 (06): : 2596 - 2600
  • [5] Hydrogen borrowing methodology: New iridium(III) catalysts for amine alkylation reactions
    Lanaro, Roberta
    Frodsham, Lianne
    Marsden, Stephen P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [6] Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology
    Hamid, M. Haniti S. A.
    Allen, C. Liana
    Lamb, Gareth W.
    Maxwell, Aoife C.
    Maytum, Hannah C.
    Watson, Andrew J. A.
    Williams, Jonathan M. J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) : 1766 - 1774
  • [7] Iron-catalyzed N-alkylation of aromatic amines via borrowing hydrogen strategy
    Chen, Hui
    Wang, Qingfu
    Liu, Tingting
    Chen, Haitao
    Zhou, Duo
    Qu, Fengbo
    JOURNAL OF COORDINATION CHEMISTRY, 2021, 74 (4-6) : 877 - 884
  • [8] Titanium-Catalyzed Selective N-Alkylation of Amines with Alcohols via Borrowing Hydrogen Methodology
    Upadhyay, Rahul
    Maurya, Sushil K.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24): : 16960 - 16966
  • [9] 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
    Liu, Pengcheng
    Lang, Ran
    Lu, Lei
    Yu, Zhentao
    Li, Feng
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (04): : 1943 - 1950
  • [10] Iron-Catalyzed N-Alkylation of Secondary Amines with Alcohols Using Borrowing Hydrogen Strategy
    Qu, Ruxin
    Cheng, Yaxuan
    Yang, Siwei
    Zhao, Chaoyu
    Liu, Huiling
    Huang, Xuri
    CHEMISTRYSELECT, 2021, 6 (17): : 4089 - 4097