doi: 10.1021/acs.joc.8b00264.
Epub 2018 Jul 2.
Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles
Affiliations
- PMID: 29882669
- DOI: 10.1021/acs.joc.8b00264
Item in Clipboard
Palladium(II)/N-Heterocyclic Carbene Catalyzed One-Pot Sequential α-Arylation/Alkylation: Access to 3,3-Disubstituted Oxindoles
J Org Chem.
.
Abstract
Rationally designed fluorene-based mono- and bimetallic Pd-PEPPSI complexes were synthesized and demonstrated to be effective for the one-pot sequential α-arylation/alkylation of oxindoles. This streamlined approach offers efficient access to functionalized 3,3-disubstituted oxindoles in excellent yields (up to 89%) under mild reaction conditions.
Similar articles
-
N-heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation of oxindoles with aryl chlorides and aerobic oxidation of the products in a one-pot procedure.Org Lett. 2013 Mar 15;15(6):1254-7. doi: 10.1021/ol400186b. Epub 2013 Mar 1. Org Lett. 2013. PMID: 23451859
-
Synthesis of 3,3-Disubstituted Oxindoles by Palladium-Catalyzed Asymmetric Intramolecular α-Arylation of Amides: Reaction Development and Mechanistic Studies.Chemistry. 2013 Sep 2;19(36):11916-27. doi: 10.1002/chem.201301572. Epub 2013 Jul 25. Chemistry. 2013. PMID: 23893893
-
Palladium-catalyzed carbonylative α-arylation of 2-oxindoles with (hetero)aryl bromides: efficient and complementary approach to 3-acyl-2-oxindoles.Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9582-6. doi: 10.1002/anie.201404217. Epub 2014 Jul 9. Angew Chem Int Ed Engl. 2014. PMID: 25044569
-
Improved catalysts for the palladium-catalyzed synthesis of oxindoles by amide alpha-arylation. Rate acceleration, use of aryl chloride substrates, and a new carbene ligand for asymmetric transformations.J Org Chem. 2001 May 18;66(10):3402-15. doi: 10.1021/jo005761z. J Org Chem. 2001. PMID: 11348123
-
Rhodium-Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3-Disubstituted Oxindoles.Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11927-11930. doi: 10.1002/anie.201704922. Epub 2017 Aug 14. Angew Chem Int Ed Engl. 2017. PMID: 28704579
Cited by
-
Transition-metal-free α-arylation of oxindoles via visible-light-promoted electron transfer.Chem Sci. 2019 Jan 22;10(10):3049-3053. doi: 10.1039/c8sc05170d. eCollection 2019 Mar 14. Chem Sci. 2019. PMID: 30996886 Free PMC article.
-
Rh(I)/(III)-N-Heterocyclic Carbene Complexes: Effect of Steric Confinement Upon Immobilization on Regio- and Stereoselectivity in the Hydrosilylation of Alkynes.Chemistry. 2021 Dec 6;27(68):17220-17229. doi: 10.1002/chem.202103099. Epub 2021 Nov 8. Chemistry. 2021. PMID: 34672398 Free PMC article.
-
Palladium-Catalyzed Chemoselective Activation of sp3 vs sp2 C-H Bonds: Oxidative Coupling To Form Quaternary Centers.ACS Catal. 2019 Apr 5;9(4):3716-3724. doi: 10.1021/acscatal.9b00091. Epub 2019 Mar 8. ACS Catal. 2019. PMID: 31777683 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
