Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

Eshani Das; Mark Aldren M. Feliciano; Pavel Yamanushkin; Xinsong Lin; Brian Gold

doi:10.1039/D3OB01559A

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Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom†

Eshani Das,

‡^b Mark Aldren M. Feliciano,

‡^ab Pavel Yamanushkin,

^b Xinsong Lin^c and Brian Gold

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico, USA
E-mail: bgold@nmsu.edu

^b Department of Chemistry and Chemical Biology, University of New Mexico, New Mexico, USA

^c Department of Chemistry and Biochemistry Florida State University, Tallahassee, FL, USA

Abstract

We report the synthesis of heterobiarylcyclooctynes bearing an endocyclic heteroatom, oxa-azabenzobenzocyclooctynes (O-ABCs). The integration of design strategies for accelerating strain-promoted azide–alkyne cycloadditions results in reactivity with organic azides that surpasses all cyclooctyne reagents reported to date. O-ABCs and related compounds provide insights into the effects of structural modifications on reactivity that can aid in the design of new reagents for click and bioorthogonal chemistry.

This article is part of the themed collection: Computational Organic Chemistry

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DOI: https://doi.org/10.1039/D3OB01559A
Article type: Paper
Submitted: 27 Sep 2023
Accepted: 11 Oct 2023
First published: 18 Oct 2023

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Org. Biomol. Chem., 2023,21, 8857-8862

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Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

E. Das, M. A. M. Feliciano, P. Yamanushkin, X. Lin and B. Gold, Org. Biomol. Chem., 2023, 21, 8857 DOI: 10.1039/D3OB01559A

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Organic & Biomolecular Chemistry

Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom†

Abstract

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Oxa-azabenzobenzocyclooctynes (O-ABCs): heterobiarylcyclooctynes bearing an endocyclic heteroatom

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