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Controllable Pd-Catalyzed Allylation of Indoles with Skipped Enynes: Divergent Synthesis of Indolenines and N-Allylindoles.

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An unprecedented acid- and ligand-controlled divergent allylation of indoles with unactivated skipped enynes via Pd hydride catalysis has been disclosed. This redox-neutral transformation went through multiple hydropalladation insertion, β-hydrogen elimination,… Click to show full abstract

An unprecedented acid- and ligand-controlled divergent allylation of indoles with unactivated skipped enynes via Pd hydride catalysis has been disclosed. This redox-neutral transformation went through multiple hydropalladation insertion, β-hydrogen elimination, π-σ-π isomerization, and allylic substitution steps. This method not only provides a platform for synthesizing indolenines and N-allylindoles but also allows facile access to functional 1,3-dienes with high atom and step economy.

Keywords: catalyzed allylation; skipped enynes; controllable catalyzed; indolenines allylindoles; allylation indoles

Journal Title: Organic letters
Year Published: 2018

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