Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones

An iridium-catalyzed C–H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C–H functionalization strategy delivers 7-borylindoles that undergo facile oxidation–hydrolysis to 7-hydroxyindoles and subsequent oxidation to the desired indole...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-03, Vol.77 (6), p.2584-2587
Main Authors: Wang, Christy, Sperry, Jonathan
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrogen Bonding
Indolequinones - chemical synthesis
Indolequinones - chemistry
Indoles - chemistry
Iridium - chemistry
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Oxidation-Reduction
Preparations and properties
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Summary:An iridium-catalyzed C–H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C–H functionalization strategy delivers 7-borylindoles that undergo facile oxidation–hydrolysis to 7-hydroxyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C–H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300330u