Trapping Reactions of Benzynes Initiated by Intramolecular Nucleophilic Addition of a Carbonyl Oxygen to the Electrophilic Aryne

Bhavani Shankar Chinta, Sahil Arora, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

We describe here reactions in which a carbonyl oxygen atom initiates cascade reactions by nucleophilic attack on a covalently attached benzyne. The benzynes are produced by thermal cyclization of triynes via hexadehydro-Diels–Alder reaction. The initially produced oxocarbenium/aryl carbanionic zwitterion is protonated in situ by an external protic nucleophile (NuH) of appropriate acidity. The resulting ion pair (oxocarbenium+/Nu) collapses through several different mechanistic manifolds, adding to the diversity of structural classes that can be generated.

Original languageEnglish (US)
Pages (from-to)425-429
Number of pages5
JournalOrganic Letters
Volume24
Issue number1
DOIs
StatePublished - Jan 14 2022

Bibliographical note

Funding Information:
This investigation was made possible with the support of the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097). Some of the NMR data were obtained using instrumentation funded by a National Institutes of Health Shared Instrumentation Grant (S10OD011952). Mass spectrometry was performed at the University of Minnesota, Masonic Cancer Center, Analytical Biochemistry Shared Resource laboratory, using instrumentation partially funded by a Cancer Center Support Grant (CA-77598). DFT calculations were performed using resources made available through the University of Minnesota Supercomputer Institute.

Publisher Copyright:
© 2021 American Chemical Society.

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