Concepedia

Synthesis of Benzannulated N-Heterocycles by a Palladium-Catalyzed C−C/C−N Coupling of Bromoalkylamines

Praew Thansandote, Manuel Raemy, Alena Rudolph, Mark Lautens

Organic Letters · 2007 · 110 citations · 18 references

DOI

Concepts

Abstract

A palladium-catalyzed domino intermolecular alkylation/intramolecular amination of functionalized aryl iodides represents a new strategy for the synthesis of benzannulated N-heterocycles, affording functionalized indolines and tetrahydroquinolines from simple precursors.

References

18

Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides

Qilong Shen, John F. Hartwig · Journal of the American Chemical Society · 2006 · 364 citations

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A New Route to Fused Aromatic Compounds by Using a Palladium-Catalyzed Alkylation - Alkenylation Sequence

Mark Lautens, Sandrine Piguel · Angewandte Chemie International Edition · 2000 · 255 citations

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Synthesis of Highly Substituted Indolines and Indoles via Intramolecular [4 + 2] Cycloaddition of Ynamides and Conjugated Enynes

Joshua R. Dunetz, Rick Danheiser · Journal of the American Chemical Society · 2005 · 182 citations · Full text

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A New Route to Fused Aromatic Compounds by Using a Palladium-Catalyzed Alkylation – Alkenylation Sequence

Mark Lautens, Sandrine Piguel · Angewandte Chemie · 2000 · 182 citations

, , +12

Toward an Improved Understanding of the Unusual Reactivity of Pd<sup>0</sup>/Trialkylphosphane Catalysts in Cross‐Couplings of Alkyl Electrophiles: Quantifying the Factors That Determine the Rate of Oxidative Addition

Ivory D. Hills, Matthew R. Netherton, Gregory C. Fu · Angewandte Chemie International Edition · 2003 · 177 citations · Full text

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