doi: 10.1021/acs.orglett.9b00122.
Epub 2019 Feb 28.
Copper-Catalyzed C-H Carbamoyloxylation of Aryl Carboxamides with CO2 and Amines at Ambient Conditions
Affiliations
- PMID: 30817162
- DOI: 10.1021/acs.orglett.9b00122
Item in Clipboard
Copper-Catalyzed C-H Carbamoyloxylation of Aryl Carboxamides with CO2 and Amines at Ambient Conditions
Org Lett.
.
Abstract
A copper-catalyzed, 8-aminoquinoline-assisted, one-pot three-component coupling of aryl carboxamides, CO2, and amines has been developed. This protocol proceeds smoothly in the presence of inexpensive CuI and MnO2 at room temperature under atmospheric CO2 pressure, leading to simultaneous construction of C-O and C-N bonds. The reaction displays a broad substrate scope, high functional group tolerance, and excellent monoselectivity, providing an operationally simple method for the synthesis of various O-aryl carbamates.
Similar articles
-
Photoredox-catalyzed coupling of aryl sulfonium salts with CO2 and amines to access O-aryl carbamates.Chem Commun (Camb). 2023 Jan 17;59(6):764-767. doi: 10.1039/d2cc06033g. Chem Commun (Camb). 2023. PMID: 36541669
-
Visible light-driven carbamoyloxylation of the α-C(sp3)-H bond of arylacetones via radical-initiated hydrogen atom transfer.Chem Commun (Camb). 2022 May 12;58(39):5845-5848. doi: 10.1039/d2cc01761j. Chem Commun (Camb). 2022. PMID: 35466975
-
Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.Acc Chem Res. 2008 Nov 18;41(11):1450-60. doi: 10.1021/ar8000298. Acc Chem Res. 2008. PMID: 18698852
-
Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.J Org Chem. 2005 Jun 24;70(13):5164-73. doi: 10.1021/jo0504464. J Org Chem. 2005. PMID: 15960520
-
Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C-N Coupling Reactions With No Additional Ligands.Front Chem. 2019 Oct 30;7:723. doi: 10.3389/fchem.2019.00723. eCollection 2019. Front Chem. 2019. PMID: 31737602 Free PMC article.
Cited by
-
Design, synthesis, and physicochemical study of a biomass-derived CO2 sorbent 2,5-furan-bis(iminoguanidine).iScience. 2021 Mar 4;24(4):102263. doi: 10.1016/j.isci.2021.102263. eCollection 2021 Apr 23. iScience. 2021. PMID: 33796847 Free PMC article.
-
Dual Nickel Photocatalysis for O-Aryl Carbamate Synthesis from Carbon Dioxide.J Org Chem. 2023 Mar 17;88(6):3822-3829. doi: 10.1021/acs.joc.3c00023. Epub 2023 Feb 27. J Org Chem. 2023. PMID: 36848485 Free PMC article.
Publication types
LinkOut - more resources
Full Text Sources
