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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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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cited_by cdi_FETCH-LOGICAL-a410t-5c8cbe47f4ca623969f1d10ef3b7c0205430e59b2bcb75954d306d654787ad1e3
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container_issue 6
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container_title Journal of organic chemistry
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creator Wang, Christy
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description 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.
doi_str_mv 10.1021/jo300330u
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
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
title Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones
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