Copper(II) Trifluoromethanesulfonate as an Efficient, Versatile, and Dual-Purpose Catalyst for the Regioselective Acetylation of <scp>l</scp> -Sorbose under Neat and Solvent-Directed Conditions

<b>Herein</b>, we report that copper-(II) trifluoromethanesulfonate [Cu-(OTf)<sub>2</sub>], a stable, versatile, and dual-purpose catalyst, efficiently catalyzed the acetylation of l-sorbose under various conditions following metal trifluoromethanesulfonate screening. Regioselectivity is critically governed by solvents: solvent-free reactions favor the open-chain <i>keto</i>-sorbopentaacetate, whereas coordinating solvents direct acetylation toward the cyclic α-l-sorbopyranosyl tetraacetate. These findings underscore the pivotal role of solvents in steering reaction pathways, enabling selective and sustainable synthesis of structurally distinct sugar derivatives while using a minimal amount of catalysts.

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Journal
ACS Omega
Published
2026-01-12
DOI
https://doi.org/10.1021/acsomega.5c11787
Primary Topic
Chemical Synthesis and Reactions
Type
article
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article

Copper(II) Trifluoromethanesulfonate as an Efficient, Versatile, and Dual-Purpose Catalyst for the Regioselective Acetylation of l -Sorbose under Neat and Solvent-Directed Conditions

Shang‐Cheng Hung, Yuan Chen, Cheng-Hsiu Chang, Jasper S. Dumalaog et al.
ACS Omega
Chemical Synthesis and Reactions
article

Copper(II) Trifluoromethanesulfonate as an Efficient, Versatile, and Dual-Purpose Catalyst for the Regioselective Acetylation of l -Sorbose under Neat and Solvent-Directed Conditions

Shang‐Cheng Hung, Yuan Chen, Cheng-Hsiu Chang, Jasper S. Dumalaog, Fu-Chen Liu
article en

Abstract

<b>Herein</b>, we report that copper-(II) trifluoromethanesulfonate [Cu-(OTf)<sub>2</sub>], a stable, versatile, and dual-purpose catalyst, efficiently catalyzed the acetylation of l-sorbose under various conditions following metal trifluoromethanesulfonate screening. Regioselectivity is critically governed by solvents: solvent-free reactions favor the open-chain <i>keto</i>-sorbopentaacetate, whereas coordinating solvents direct acetylation toward the cyclic α-l-sorbopyranosyl tetraacetate. These findings underscore the pivotal role of solvents in steering reaction pathways, enabling selective and sustainable synthesis of structurally distinct sugar derivatives while using a minimal amount of catalysts.

ACS OmegaVol. 11(3)
National Taitung University (TW), National Tsing Hua University (TW), National Dong Hwa University (TW), Genomics Research Center, Academia Sinica (TW), Institute of Molecular Biology and Biophysics (RU), Academia Sinica (TW), National Cheng Kung University (TW)
Responsible consumption and production
Openalex Percentile: Top 90%
Chemical Synthesis and Reactions
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Copper(II) Trifluoromethanesulfonate as an Efficient, Versatile, and Dual-Purpose Catalyst for the Regioselective Acetylation of <scp>l</scp> -Sorbose under Neat and Solvent-Directed Conditions — Shang‐Cheng Hung, Yuan Chen, et al. · ACS Omega (2026) | TGRS Research Map | TGRS