Recent advances in catalysts for the Henry reaction
The Henry reaction, the coupling of a nitro alkane and a carbonyl group, is an important C–C bond-forming reaction giving nitro alkanols, which are useful, versatile intermediates in synthetic organic chemistry and for the pharmaceutical industry. Among the catalysts employed in the Henry reaction,...
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| Published in | Australian journal of chemistry Vol. 75; no. 10; pp. 806 - 819 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Collingwood
CSIRO
08.11.2022
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| Subjects | |
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| Abstract | The Henry reaction, the coupling of a nitro alkane and a carbonyl group, is an important C–C bond-forming reaction giving nitro alkanols, which are useful, versatile intermediates in synthetic organic chemistry and for the pharmaceutical industry. Among the catalysts employed in the Henry reaction, transition metal complex catalysts play an important role. Transition metal complexes, including small molecules and nanoparticles, catalyze the asymmetric Henry reaction efficiently and in most of the cases give chiral nitro alkanol products in good yield and enantiomeric excess. This review summarizes transition metal complex catalysts, metal-free organic catalysts and nanoparticle catalysts for the Henry reaction. |
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| AbstractList | The Henry reaction, the coupling of a nitro alkane and a carbonyl group, is an important C–C bond-forming reaction giving nitro alkanols, which are useful, versatile intermediates in synthetic organic chemistry and for the pharmaceutical industry. Among the catalysts employed in the Henry reaction, transition metal complex catalysts play an important role. Transition metal complexes, including small molecules and nanoparticles, catalyze the asymmetric Henry reaction efficiently and in most of the cases give chiral nitro alkanol products in good yield and enantiomeric excess. This review summarizes transition metal complex catalysts, metal-free organic catalysts and nanoparticle catalysts for the Henry reaction. |
| Author | Li, Xu Xiao, Wei Bao, Xuefei Chen, Guoliang Jiang, Chunfeng |
| Author_xml | – sequence: 1 givenname: Xuefei orcidid: 0000-0002-4457-196X surname: Bao fullname: Bao, Xuefei – sequence: 2 givenname: Xu surname: Li fullname: Li, Xu – sequence: 3 givenname: Chunfeng surname: Jiang fullname: Jiang, Chunfeng – sequence: 4 givenname: Wei surname: Xiao fullname: Xiao, Wei – sequence: 5 givenname: Guoliang surname: Chen fullname: Chen, Guoliang |
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and -1-nitro-2-phenylcyclohexane using W-2 Raney nickel catalyst. publication-title: J Org Chem doi: 10.1021/jo01059a073 – volume: 2012 start-page: 3059 year: 2012 ident: CH22136R24 article-title: Biocatalytic approaches to the Henry (nitroaldol) reaction. publication-title: Eur J Org Chem doi: 10.1002/ejoc.201101840 – volume: 50 start-page: 6623 year: 2014 ident: CH22136R31 article-title: (2,5)-2-methylaminomethyl-1-methyl-5-phenylpyrrolidine, a chiral diamine ligand for copper(ii)-catalysed Henry reactions with superb enantiocontrol. publication-title: Chem Commun doi: 10.1039/c4cc02429j – volume: 25 start-page: 2101 year: 2020 ident: CH22136R45 article-title: Synthesis and catalytic application of two mononuclear complexes bearing diethylenetriamine derivative ligand. publication-title: Molecules doi: 10.3390/molecules25092101 – volume: 56 start-page: 1969 year: 2021 ident: CH22136R35 article-title: Conjugates of bispidine and monoterpenoids as ligands of metal complex catalysts for the Henry reaction. publication-title: Russ J Org Chem doi: 10.1134/s1070428020110123 – volume: 51 start-page: 1019 year: 2022 ident: CH22136R62 article-title: Halogen bonding in cadmium(ii) MOFs: its influence on the structure and on the nitroaldol reaction in aqueous medium. publication-title: Dalton Trans doi: 10.1039/d1dt03755b – volume: 16 start-page: 449 year: 2019 ident: CH22136R3 article-title: Highly efficient Michael reactions of nitroolefins by grinding means. publication-title: Curr Org Synth doi: 10.2174/1570179416666190101122150 – volume: 72 start-page: 153090 year: 2021 ident: CH22136R37 article-title: C2 symmetric copper (II) complexes of l-valine and l-phenyl alanine based chiral diimines for catalytic asymmetric Henry reaction. publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2021.153090 – volume: 29 start-page: 445 year: 2021 ident: CH22136R25 article-title: Research progress on chiral metal‐catalyzed for asymmetric Henry reaction. publication-title: Chin J Syn Chem doi: 10.15952/j.cnki.cjsc.1005-1511.21017 – volume: 17 start-page: 297 year: 2020 ident: CH22136R26 article-title: Advances in Henry reaction: a versatile method in organic synthesis. publication-title: Mini Rev Org Chem doi: 10.2174/1570193x16666190214150144 – volume: 5 start-page: 6532 year: 2020 ident: CH22136R65 article-title: Highly efficient nanosized mesoporous CuMgAl ternary oxide catalyst for nitro-alcohol synthesis: ultrasound-assisted sustainable green perspective for the Henry reaction. publication-title: ACS Omega doi: 10.1021/acsomega.9b04212 – volume: 57 start-page: 915 year: 2001 ident: CH22136R7 article-title: The Henry reaction: recent examples. publication-title: Tetrahedron doi: 10.1016/s0040-4020(00)00965-0 – volume: 1 start-page: 1529 year: 2011 ident: CH22136R30 article-title: Cu(II)-macrocylic [H]salen catalyzed asymmetric nitroaldol reaction and its application in the synthesis of α1-adrenergic receptor agonist ()-phenylephrine. publication-title: ACS Catal doi: 10.1021/cs2004467 – volume: 161 start-page: 104868 year: 2021 ident: CH22136R58 article-title: Polymeric nanoassembly of imine functionalized magnetite for loading copper salts to catalyze Henry and A-coupling reactions. publication-title: React Funct Polym doi: 10.1016/j.reactfunctpolym.2021.104868 – volume: 61 start-page: 152485 year: 2020 ident: CH22136R57 article-title: Amino acids derived chiral bifunctional (thio)urea tertiary-amines catalyzed asymmetric Henry reaction of trifluoromethy ketones. publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2020.152485 – volume: 131 start-page: 10872 year: 2009 ident: CH22136R4 article-title: Catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes with nitroalkenes: backbone fluorination improves selectivity. publication-title: J Am Chem Soc doi: 10.1021/ja904375q – volume: 58 start-page: 593 year: 2010 ident: CH22136R50 article-title: Development of chiral thiourea catalysts and its application to asymmetric catalytic reactions. publication-title: Chem Pharm Bull doi: 10.1248/cpb.58.593 |
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