We report a phosphine-mediated cyclodehydration procedure for the facile synthesis of -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.
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Synthesis of Hydrazonyl Sultones via Phosphine-Mediated Cyclodehydration of Vicinal Sulfo-acyl Hydrazides.
Org Lett
October 2024
Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260-3000, United States.
We report a phosphine-mediated cyclodehydration procedure for the facile synthesis of -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.
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Chembiochem
July 2023
Department of Chemistry, State University of New York at Buffalo, Buffalo, NY, 14260-3000, USA.
We report the synthesis of a series of hydrazonyl sultones (HS) containing an ortho-CF group, a five- or six-membered sultone ring, and a varying N-aryl substituent, and characterization of their aqueous stability and reactivity toward bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN) in a 1,3-dipolar cycloaddition reaction.
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J Am Chem Soc
May 2023
Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260-3000, United States.
Here we report the design and synthesis of a new class of bioorthogonal reagents called hydrazonyl sultones (HS) that serve as stable tautomers of highly reactive nitrile imines (NI). Compared to the photogenerated NI, HS display a broad range of aqueous stability and tunable reactivity in a 1,3-dipolar cycloaddition reaction, depending on substituents, sultone ring structure, and solvent conditions. DFT calculations have provided vital insights into the HS → NI tautomerism, including a base-mediated anionic tautomerization pathway and a small activation barrier.
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