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Regioselective synthesis of tetrahydroquinolines via syn- and anti-nucleopalladation-initiated cascade processes

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Abstract

Palladium(II)-catalyzed regioselective syn-chloropalladation and anti-acetoxypalladation-initiated cascade processes were developed for the synthesis of functionalized tetrahydroquinolines. A series of N-propargyl arylamines tethered with an α,β-unsaturated carbonyl scaffold underwent atom economical cascade reactions to deliver chloro- and acetoxy-substituted tetrahydroquinolines bearing an exocyclic double bond in high yields. A mechanism is proposed for these cascade processes involving a sequential syn-chloropalladation or anti-acetoxypalladation of alkynes followed by intramolecular olefin insertion (6-exo-trig) and protonolysis steps. The reaction was completely regioselective and the terminal aryl/alkyl group of the propargyl moiety dictated the regiochemistry of the initial nucleopalladation. The role of the bidentate nitrogen ligand is crucial to trigger the acetoxypalladation-initiated cascade sequence in contrast to the chloropalladation-initiated process.

Graphical abstract: Regioselective synthesis of tetrahydroquinolines via syn- and anti-nucleopalladation-initiated cascade processes

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Article information


Submitted
06 Sep 2020
Accepted
05 Oct 2020
First published
05 Oct 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Regioselective synthesis of tetrahydroquinolines via syn- and anti-nucleopalladation-initiated cascade processes

M. Karuppasamy, P. Vinoth, N. Pradeep, S. Nagarajan, C. U. Maheswari and V. Sridharan, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB01840F

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