Copper(II) Trifluoromethanesulfonate as an Efficient, Versatile, and Dual-Purpose Catalyst for the Regioselective Acetylation of l‑Sorbose under Neat and Solvent-Directed Conditions
Yu-An Chen, Jasper S. Dumalaog, Cheng-Hsiu Chang, Fu-Chen Liu, Shang-Cheng Hung
TL;DR
Copper(II) trifluoromethanesulfonate efficiently and selectively catalyzes the acetylation of l-sorbose under different solvent conditions.
Contribution
A dual-purpose catalyst enables regioselective acetylation of l-sorbose with solvent-controlled outcomes.
Findings
Copper(II) trifluoromethanesulfonate catalyzes acetylation of l-sorbose efficiently.
Solvent-free conditions favor open-chain products, while coordinating solvents favor cyclic derivatives.
The catalyst enables selective and sustainable synthesis of sugar derivatives.
Abstract
Herein, we report that copper(II) trifluoromethanesulfonate [Cu(OTf)2], 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 keto-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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Taxonomy
TopicsChemical Synthesis and Reactions · Carbon dioxide utilization in catalysis · Sulfur-Based Synthesis Techniques