Work

Synthesis of Hydrazonyl Sultones via Phosphine-Mediated Cyclodehydration of Vicinal Sulfo-acyl Hydrazides

Year: 2024

Type: article

Abstract: We report a phosphine-mediated cyclodehydration procedure for the facile synthesis of N -aryl/alkyl-substituted hydrazonyl sultones, a class of bioorthogonal reagents, from the readily prepared vicinal sulfo-acyl hydrazides in moderate to good yields. The aqueous stability and bioorthogonal reactivity of these hydrazonyl sultones toward bicyclo[6.1.0]non-4-yn-9-ylmethanol were investigated, revealing key structural requirements for hydrazonyl sultones to possess balanced stability and reactivity.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02687

Authors: Balasaheb R. Borade, Ming Fang, Qing Lin

Institution: University at Buffalo, State University of New York

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Award: Development and Applications of Bioorthogonal Chemistry