Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles
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nihms-1681499.pdf
Description
Accepted version
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1.27 MB
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Author(s)
Knippel, James Levi
Ye, Yuxuan
Buchwald, Stephen L.
Date Issued
March 2021
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Knippel, James Levi, Ye, Yuxuan and Buchwald, Stephen L. 2021. "Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles." Organic Letters, 23 (6).
Version
Author's final manuscript
Abstract
Although substituted benzimidazoles are common substructures in bioactive small molecules, synthetic methods for their derivatization are still limited. Previously, several enantioselective allylation reactions of benzimidazoles were reported that functionalize the nucleophilic nitrogen atom. Herein we describe a reversal of this inherent selectivity toward N-allylation by using electrophilic N-OPiv benzimidazoles with readily available 1,3-dienes as nucleophile precursors. This CuH-catalyzed approach utilizes mild reaction conditions, exhibits broad functional-group compatibility, and exclusively forms the C2-allylated product with excellent stereoselectivity.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.1c00306
