Concepedia

Palladium-Catalyzed Coupling of 3-Indolyl Triflate. Syntheses of 3-Vinyl and 3-Alkynylindoles

Synthetic Communications · 1992 · 45 citations · 32 references

Concepts

Palladium-catalyzed CouplingChemical EngineeringCross-coupling Reaction3-Indolyne 22EngineeringNatural Sciences2-Trimethylsilyl-3-indolyl Triflate 20Diversity-oriented SynthesisOrganic ChemistryOrganometallic CatalysisCatalysisChemistrySynthetic ChemistryAbstract Palladium-catalyzed Coupling

Abstract

Abstract Palladium-catalyzed coupling of 1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkynes gives 3-vinyl (2) and 3-alkynylindoles in 45—93% yields. An attempt to generate 2, 3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).

References

32

Pure appl. Chem

Gerhard Habermehl · Toxicon · 1983 · 3.1K citations

Chemical Measurement, Engineering, Pure Appl +4

FLUORIDE-INDUCED 1,2-ELIMINATION OF <i>O</i>-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS

Yoshio Himeshima, Takaaki Sonoda, Hiroshi Kobayashi · Chemistry Letters · 1983 · 915 citations

Halogenation, Abstract Fluoride-induced 1,2-Elimination, O-trimethylsilylphenyl Triflate +6

Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. Approaches to ergot alkaloids

Peter J. Harrington, Louis S. Hegedus · The Journal of Organic Chemistry · 1984 · 188 citations

4-Substituted Indoles, Engineering, Natural Sciences +11

Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. 2. Total synthesis of the N-acetyl methyl ester of (.+-.)-clavicipitic acids

Peter J. Harrington, Louis S. Hegedus, Keith F. McDaniel · Journal of the American Chemical Society · 1987 · 187 citations

4-Substituted Indoles, Engineering, Altmetric Attention Score +10

Hetarynes

Manfred G. Reinecke · Tetrahedron · 1982 · 146 citations