C3-Functionalization of indoles with α-heteroaryl-substituted methyl alcohols
Literature Information
Ethan J. Pazur, Nikhil R. Tasker, Peter Wipf
The transition metal-free Cs2CO3/Oxone®-mediated C3-alkylation of indoles proceeds in moderate to high yields with a variety of C4–C7 functionalized indoles and is applicable to 2-, 3- and 4-hydroxymethyl pyridines and related electron-deficient heterocycles, permitting novel late-stage drug functionalizations. Preliminary mechanistic studies support a hydrogen autotransfer-type chain process starting with an initial oxidation of the alcohol to the corresponding aldehyde, followed by a subsequent condensation onto indole and reduction/hydride delivery from another equivalent of the primary alcohol.
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Source Journal
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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