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Weak Coordination Enabled Switchable C4-Alkenylation and Alkylation of Indoles with Allyl Alcohols

Sourav Pradhan, Manmath Mishra, Pinaki Bhusan De, Sonbidya Banerjee, Tharmalingam Punniyamurthy

2020Organic Letters64 citationsDOI

Abstract

A weak carbonyl coordination facilitated tunable reactivity between alkenylation and alkylation of indoles at the C4 C-H site is presented using readily accessible allylic alcohols in the presence of Rh catalysis by switching the additives or directing group. Exclusive site selectivity, functional group tolerance, and late-stage modifications are the important practical features.

Topics & Concepts

ChemistryAlkylationOrganic chemistryAllyl alcoholCombinatorial chemistryMedicinal chemistryCatalysisCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions
Weak Coordination Enabled Switchable C4-Alkenylation and Alkylation of Indoles with Allyl Alcohols | Litcius