Issue 44, 2023

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Sep 2023
Accepted
11 Oct 2023
First published
18 Oct 2023

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

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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