Synthesis of tertiary amines by direct Bronsted acid catalyzed reductive amination

被引:20
作者
Hussein, Mohanad A. [1 ]
Dinh, An H. [1 ]
Huynh, Vien T. [2 ]
Thanh Vinh Nguyen [1 ]
机构
[1] Univ New South Wales, Sch Chem, Sydney, NSW, Australia
[2] Univ Sydney, Sch Chem, Sydney, NSW, Australia
基金
澳大利亚研究理事会;
关键词
TRIFLIC ACID; EFFICIENT; ALDEHYDES; KETONES; N; N-DIMETHYLFORMAMIDE; HYDROGENATION; FORMAMIDES; AMIDATION; ALCOHOLS;
D O I
10.1039/d0cc02955f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tertiary amines are ubiquitous and valuable compounds in synthetic chemistry, with a wide range of applications in organocatalysis, organometallic complexes, biological processes and pharmaceutical chemistry. One of the most frequently used pathways to synthesize tertiary amines is the reductive amination reaction of carbonyl compounds. Despite developments of numerous new reductive amination methods in the past few decades, this reaction generally requires non-atom-economic processes with harsh conditions and toxic transition-metal catalysts. Herein, we report simple yet practical protocols using triflic acid as a catalyst to efficiently promote the direct reductive amination reactions of carbonyl compounds on a broad range of substrates. Applications of this new method to generate valuable heterocyclic frameworks and polyamines are also included.
引用
收藏
页码:8691 / 8694
页数:4
相关论文
共 57 条
[1]   Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].
AbdelMagid, AF ;
Carson, KG ;
Harris, BD ;
Maryanoff, CA ;
Shah, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862
[2]   Recent Advances in Reductive Amination Catalysis and Its Applications [J].
Alinezhad, Heshmatollah ;
Yavari, Hossein ;
Salehian, Fatemeh .
CURRENT ORGANIC CHEMISTRY, 2015, 19 (11) :1021-1049
[3]   Fluorinated Alcohols: Magic Reaction Medium and Promoters for Organic Synthesis [J].
An, Xiao-De ;
Xiao, Jian .
CHEMICAL RECORD, 2020, 20 (02) :142-161
[4]   PREPARATION OF TERTIARY N,N-DIMETHYLAMINES BY LEUCKART REACTION [J].
BACH, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1647-&
[5]   Microwave-assisted conversion of carbonyl compounds into formylated secondary amines: new contribution to the Leuckart reaction mechanism in N-methylformamide [J].
Barba, Fructuoso ;
Recio, Javier ;
Batanero, Belen .
TETRAHEDRON LETTERS, 2013, 54 (14) :1835-1838
[6]   Fluorinated alcohols:: A new medium for selective and clean reaction [J].
Bégué, JP ;
Bonnet-Delpon, D ;
Crousse, B .
SYNLETT, 2004, (01) :18-29
[7]   Rapid Organocatalytic Formation of Carbon Monoxide: Application towards Carbonylative Cross Couplings [J].
Ben Zoller ;
Zapp, Josef ;
Huy, Peter H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (43) :9632-9638
[8]   EXTENSION OF THE LEUCKART SYNTHESIS OF TERTIARY AMINES, INCLUDING ITS APPLICATION TO ALPHA,BETA-UNSATURATED CARBONYL COMPOUNDS [J].
BUNNETT, JF ;
MARKS, JL ;
MOE, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (04) :985-987
[9]   Hexafluoroisopropanol as a highly versatile solvent [J].
Colomer, Ignacio ;
Chamberlain, Anna E. R. ;
Haughey, Maxwell B. ;
Donohoe, Timothy J. .
NATURE REVIEWS CHEMISTRY, 2017, 1 (11)
[10]   2,2,2-Trifluoroethanol as Green Solvent in Organic Synthesis: A Review [J].
Dandia, Anshu ;
Singh, Ruby ;
Joshi, Jyoti ;
Kumari, Sukhbeer .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2014, 11 (04) :462-476