Green imine synthesis from amines using transition metal and micellar catalysis

被引:10
作者
Park, Luke H. [1 ,2 ]
Leitao, Erin M. [1 ,2 ]
Weber, Cameron C. [1 ,2 ]
机构
[1] Univ Auckland, Sch Chem Sci, Private Bag 92019, Auckland 1142, New Zealand
[2] Victoria Univ Wellington, MacDiarmid Inst Adv Mat & Nanotechnol, Wellington 6012, New Zealand
关键词
LIFE-CYCLE ASSESSMENT; AEROBIC OXIDATION; SECONDARY-AMINES; SELECTIVE OXIDATION; BENZYL AMINES; SCHIFF-BASES; PENICILLIN; PALLADIUM; EARTH; DEHYDROGENATION;
D O I
10.1039/d3ob01730c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Imines are a versatile class of chemicals with applications in pharmaceuticals and as synthetic intermediates. While imines are conventionally synthesized via aldehyde-amine condensation, their direct preparation from amines can avoid the need for the independent preparation of the aldehyde coupling partner and associated constraints with regard to aldehyde storage and purification. The direct preparation of imines from amines typically utilizes transition metal catalysis and is often well-aligned with green chemistry principles. This review provides a comprehensive overview of transition metal catalysed imine synthesis, with a particular focus on the copper-catalyzed oxidative coupling of amines. The emerging application of micellar catalysis for imine synthesis is also surveyed due to its potential to avoid the use of hazardous solvents and intensify these reactions through reduced catalyst loadings and locally increased reactant concentrations. Future directions relating to the confluence of these two areas are proposed towards the more sustainable preparation of imines. The direct synthesis of imines from amines using transition metal catalysis is surveyed alongside the use of micellar media. The potential for the future convergence of these approaches towards more sustainable imine synthesis is discussed.
引用
收藏
页码:202 / 227
页数:26
相关论文
共 94 条
[1]   Electron Microscopy Study of Gold Nanoparticles Deposited on Transition Metal Oxides [J].
Akita, Tomoki ;
Kohyama, Masanori ;
Haruta, Masatake .
ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (08) :1773-1782
[2]   Highly Active and Selective Ru-PNH Catalyst in Aerobic Oxidation of Benzyl Amines [J].
Aman, Michal ;
Tremmel, Jakub ;
Dostal, Libor ;
Erben, Milan ;
Tydlitat, Jiri ;
Jansa, Josef ;
Jambor, Roman .
CHEMCATCHEM, 2019, 11 (18) :4624-4630
[3]  
Anastas PT, 1998, GREEN CHEMISTRY, P1
[4]   SYNTHESIS OF PENICILLIN - 6-AMINOPENICILLANIC ACID IN PENICILLIN FERMENTATIONS [J].
BATCHELOR, FR ;
DOYLE, FP ;
NAYLER, JHC ;
ROLINSON, GN .
NATURE, 1959, 183 (4656) :257-258
[5]   A review of limit values and hazard communication standards for nickel [J].
Bates H.K. .
Metal Finishing, 2010, 108 (01) :28-32
[6]   Setting evidence-based occupational exposure limits for manganese [J].
Bevan, Ruth ;
Ashdown, Lini ;
McGough, Doreen ;
Huici-Montagud, Alicia ;
Levy, Leonard .
NEUROTOXICOLOGY, 2017, 58 :238-248
[7]   Dehydrogenation of amines to nitriles in aqueous micelles [J].
Biondini, D ;
Brinchi, L ;
Germani, R ;
Goracci, L ;
Savelli, G .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (14) :3060-3063
[8]   Aerobic Oxidation of Amines to Imines by Cesium-Promoted Mesoporous Manganese Oxide [J].
Biswas, Sourav ;
Dutta, Biswanath ;
Mullick, Kankana ;
Kuo, Chung-Hao ;
Poyraz, Altug S. ;
Suib, Steven L. .
ACS CATALYSIS, 2015, 5 (07) :4394-4403
[9]   Life cycle assessment of an industrial-scale vanadium flow battery [J].
Blume, Nick ;
Becker, Maik ;
Turek, Thomas ;
Minke, Christine .
JOURNAL OF INDUSTRIAL ECOLOGY, 2022, 26 (05) :1796-1808
[10]   Ancistrotanzanine C and related 5,1′- and 7,3′-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis [J].
Bringmann, G ;
Dreyer, M ;
Faber, JH ;
Dalsgaard, PW ;
Staerk, D ;
Jaroszewski, JW ;
Ndangalasi, H ;
Mbago, F ;
Brun, R ;
Christensen, SB .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (05) :743-748