Solid-phase rhodium carbenoid N-H insertion reactions: the synthesis of a diverse array of indoles

Journal of Combinatorial Chemistry
Sang-Hyeup LeeKim D Janda

Abstract

A solid-phase synthesis of an array of indoles is reported. The key step in our approach involves a N-H insertion reaction of N-alkylanilines into a highly reactive polymer-bound rhodium carbenoid intermediate to yield the corresponding alpha-arylamino-beta-ketoester. These insertion products were then treated under acid-catalyzed cyclodehydration conditions to yield a series of polymer-bound indole esters, which were subsequently cleaved from the resin under Lewis acid-promoted amidation conditions to yield the desired indoles in good yields and with excellent purities.

Citations

Aug 20, 2009·Journal of Combinatorial Chemistry·Nadezda Pudelová, Viktor Krchnák
Sep 15, 2009·Journal of Combinatorial Chemistry·Shilpa A WorlikarRichard C Larock
May 7, 2004·Organic Letters·Longwu QiKim D Janda
Jul 31, 2009·Organic & Biomolecular Chemistry·Samantha M Frawley CassJetze J Tepe
Feb 4, 2014·Chemical Science·Z Jane WangFrances H Arnold
Jul 2, 2014·Chemical Communications : Chem Comm·Balaji L Korbad, Sang-Hyeup Lee

Related Concepts

Catalysis
Cyclization
Indoles
Dental Resins
Rhodium

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