Pd(0)-catalyzed alkenylation and allylic dearomatization reactions between nucleophile-bearing indoles and propargyl carbonate
- PMID: 24992703
- DOI: 10.1021/ol501704q
Pd(0)-catalyzed alkenylation and allylic dearomatization reactions between nucleophile-bearing indoles and propargyl carbonate
Abstract
Spiroindolenine derivatives were synthesized by intermolecular Pd-catalyzed dearomatization of indoles. The reaction between nucleophile bearing indoles and propargyl carbonate proceeds in a cascade fashion providing spiroindolenines or spiroindolines in good to excellent yields.
Similar articles
-
Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate.Org Lett. 2014 Jul 3;16(13):3480-3. doi: 10.1021/ol501409a. Epub 2014 Jun 25. Org Lett. 2014. PMID: 24964382 Free PMC article.
-
Palladium(0)-catalyzed dearomative arylation of indoles: convenient access to spiroindolenine derivatives.Org Lett. 2012 Jul 20;14(14):3772-5. doi: 10.1021/ol301663h. Epub 2012 Jul 12. Org Lett. 2012. PMID: 22783995
-
Gold-Catalyzed Intramolecular Dearomatization Reactions of Indoles for the Synthesis of Spiroindolenines and Spiroindolines.Org Lett. 2020 Feb 21;22(4):1233-1238. doi: 10.1021/acs.orglett.9b03988. Epub 2019 Dec 2. Org Lett. 2020. PMID: 31789039
-
Development of palladium-catalyzed transformations using propargylic compounds.Chem Pharm Bull (Tokyo). 2012;60(3):285-99. doi: 10.1248/cpb.60.285. Chem Pharm Bull (Tokyo). 2012. PMID: 22382407 Review.
-
Synthesis of Spirocyclic Indolenines.Chemistry. 2016 Feb 24;22(9):2856-81. doi: 10.1002/chem.201503835. Epub 2015 Dec 14. Chemistry. 2016. PMID: 26661053 Review.
Cited by
-
From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis.Chemistry. 2016 May 4;22(19):6496-500. doi: 10.1002/chem.201600823. Epub 2016 Mar 23. Chemistry. 2016. PMID: 26918778 Free PMC article.
-
Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.J Am Chem Soc. 2017 Aug 9;139(31):10641-10644. doi: 10.1021/jacs.7b05893. Epub 2017 Jul 25. J Am Chem Soc. 2017. PMID: 28742333 Free PMC article.
-
Synthesis of Substituted 1,4-Benzodiazepines by Palladium-Catalyzed Cyclization of N-Tosyl-Disubstituted 2-Aminobenzylamines with Propargylic Carbonates.Molecules. 2025 Jul 17;30(14):3004. doi: 10.3390/molecules30143004. Molecules. 2025. PMID: 40733270 Free PMC article.
-
Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles.Org Lett. 2016 Feb 19;18(4):740-3. doi: 10.1021/acs.orglett.5b03708. Epub 2016 Jan 29. Org Lett. 2016. PMID: 26824482 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources