Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-Pot Formal Dehydroboration Sequence

Authors

Shubhendu S. Karandikar, Portland State University
Bryan E. Metze, Portland State University
Riley A. Roberts, Portland State University
David R. Stuart, Portland State UniversityFollow

Sponsor

This work was supported by the National Science Foundation under Grant No. 2247802. The NSF provided instrument funding for the BioAnalytical Mass Spectrometry Facility at PSU under Grant No. 1828753.

Published In

Organic Letters

Document Type

Citation

Publication Date

8-23-2023

Abstract

Arylboron compounds are widely available and synthetically useful reagents in which the boron group is typically substituted. Herein, we show that the boron group and -hydrogen atom are substituted in a formal cycloaddition reaction. This transformation is enabled by a one-pot sequence involving diaryliodonium and aryne intermediates. The scope of arylboron reagents and arynophiles is demonstrated, and the method is applied to the formal synthesis of an investigational drug candidate.

Rights

© American Chemical Society

Locate the Document

https://doi.org/10.1021/acs.orglett.3c02379

DOI

10.1021/acs.orglett.3c02379

Persistent Identifier

https://archives.pdx.edu/ds/psu/40759

Publisher

American Chemical Society

Citation Details

Karandikar, S. S., Metze, B. E., Roberts, R. A., & Stuart, D. R. (2023). Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-pot Formal Dehydroboration Sequence. Organic Letters.