CuH-Catalyzed Selective N-Methylation of Amines Using Paraformaldehyde as a C1 Source.
Journal
ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658
Informations de publication
Date de publication:
22 Aug 2023
22 Aug 2023
Historique:
received:
18
06
2023
accepted:
31
07
2023
medline:
28
8
2023
pubmed:
28
8
2023
entrez:
28
8
2023
Statut:
epublish
Résumé
Copper hydride (CuH) complexes have been proposed as key intermediates in synthesis and catalysis. Herein, we developed a highly efficient strategy for CuH-catalyzed N-methylation of aromatic and aliphatic amines using paraformaldehyde and polymethylhydrosiloxane (PMHS) under mild reaction conditions. The reaction proceeded smoothly without additives to furnish the corresponding N-methylated products using cyclic(alkyl)(amino)carbene (CAAC)CuH as a reaction intermediate, which results from a reaction between PMHS and (CAAC)CuCl.
Identifiants
pubmed: 37636962
doi: 10.1021/acsomega.3c04332
pmc: PMC10448681
doi:
Types de publication
Journal Article
Langues
eng
Pagination
30640-30645Informations de copyright
© 2023 The Authors. Published by American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
Références
Chem Commun (Camb). 2017 May 17;53(40):5542-5545
pubmed: 28470246
Angew Chem Int Ed Engl. 2020 May 4;59(19):7591-7597
pubmed: 32065840
Chem Sci. 2021 Aug 3;12(36):12174-12180
pubmed: 34667583
J Am Chem Soc. 2017 Jun 14;139(23):7753-7756
pubmed: 28541687
J Am Chem Soc. 2017 Jun 21;139(24):8126-8129
pubmed: 28565905
Chem Rev. 2008 Aug;108(8):2916-27
pubmed: 18616323
Cell. 2007 Feb 23;128(4):635-8
pubmed: 17320500
Chem Rev. 2020 Sep 9;120(17):9583-9674
pubmed: 32812752
Chemistry. 2016 Nov 7;22(46):16489-16493
pubmed: 27766690
Org Lett. 2015 May 15;17(10):2530-3
pubmed: 25915546
Angew Chem Int Ed Engl. 2007;46(4):498-504
pubmed: 17072922
Dalton Trans. 2015 Nov 7;44(41):18138-44
pubmed: 26420462
Angew Chem Int Ed Engl. 2018 May 14;57(20):5867-5870
pubmed: 29504659
Chem Rev. 2011 Sep 14;111(9):5215-46
pubmed: 21631125
Chemistry. 2014 Jan 13;20(3):839-45
pubmed: 24338833
Chemistry. 2015 Nov 16;21(47):16759-63
pubmed: 26450368
J Am Chem Soc. 2018 Jan 17;140(2):606-609
pubmed: 29283578
Chem Commun (Camb). 2013 May 25;49(42):4782-4
pubmed: 23598425
Chem Rev. 2011 Nov 9;111(11):7157-259
pubmed: 21830756
Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9336-9340
pubmed: 29901244
Angew Chem Int Ed Engl. 2021 May 17;60(21):11730-11734
pubmed: 33694252
Chem Commun (Camb). 2016 May 5;52(39):6545-8
pubmed: 27101227
Nat Rev Clin Oncol. 2020 Nov;17(11):655-656
pubmed: 32732909
Org Lett. 2017 Mar 17;19(6):1490-1493
pubmed: 28263072
Chem Commun (Camb). 2019 Apr 7;55(27):3915-3918
pubmed: 30869666
Acc Chem Res. 2008 Oct;41(10):1331-42
pubmed: 18636716