Hydroamination of Cyclooctynes With Primary Hydroxylamines : A new Reaction In The Click Toolbox

ChemRxiv 2026 Preprint Open access

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Authors: Vivien Herrscher, Agathe Martinez, Jean‐Bernard Behr
DOI: 10.26434/chemrxiv.15002347/v1
Cited by: 1

Abstract

Herein, we report a rapid and efficient conjugation of primary hydroxylamines with cyclooctynes. A range of R–NHOH substrates, including amino acid- and sugar-derived hydroxylamines, react readily with BCN to afford the corresponding adducts in good yields. Evaluation of various cyclooctynes revealed significant differences in reactivity, with DBCO-acid exhibiting the highest rate (k2 > 23 M-1 s-1).

Fields of Study & Subjects

Click Chemistry and Applications Catalytic Alkyne Reactions Cyclopropane Reaction Mechanisms

Publication details

Journal / source
ChemRxiv
Publisher
American Chemical Society (ACS)
Publication date
24 April 2026
Language
EN
Document type
Preprint