The Diverse Applications of Sodium l-Ascorbate as a Reducing Agent in Organic Synthesis

Abstract

Sodium l-ascorbate is an inexpensive and non-hazardous organic salt derived from ascorbic acid that is widely applied as a reducing agent in diverse industrial processes and occurs naturally in some plants and animals. In organic synthesis it can participate in a variety of reactions, playing different roles as a secondary or main reactant to promote a wide range of chemical transformations, being most commonly used along with metallic catalysts. This graphical review highlights some of the numerous applications of sodium ascorbate as a reactant in organic reactions.

Key words

sodium l-ascorbate - reduction - catalysis - photocatalysis - synthesis

Biosketches

Letícia Ribeiro Magalhães received her chemistry degree from the Federal University of Rio Grande do Norte in 2019. Currently, she is a pharmacy student and an undergraduate researcher at the same institution under the supervision of Prof. A. K. Jordão and Prof. E. G. Barbosa. Her work involves the synthesis of potentially bioactive heterocyclic compounds.

Euzebio Guimarães Barbosa received his Ph.D. in chemistry from Campinas University (UNICAMP) in 2011 under the supervision of Prof. Marcia Miguel Castro Ferreira. Currently he is a professor at the Federal University of Rio Grande do Norte. His research interests focus on medicinal chemistry and computer-aided drug design.

Alessandro Kappel Jordão received his Ph.D. in chemistry from Fluminense Federal University (UFF) in 2010 under the supervision of Prof. Vitor Francisco Ferreira and Prof. Anna Claudia. Currently, he is a professor at the Federal University of Rio Grande do Norte. His research interests focus on the synthesis of heterocyclic compounds.

Sodium l-ascorbate is an organic sodium salt that occurs as a white to slightly yellowish powder, is readily soluble in water and is only very slightly soluble in ethanol. In aqueous solutions it exhibits pH values of 5.6 to 7.0 or higher.[1] It can be obtained by dissolution of ascorbic acid (vitamin C) in water followed by the addition of an equivalent amount of sodium bicarbonate, which generates effervescence. Upon completion of the effervescence, sodium ascorbate can be precipitated by the addition of isopropanol (Scheme [1]).[2]

Scheme 1 Formation of sodium l-ascorbate from ascorbic acid

Being an inexpensive, environmentally friendly and non-hazardous compound, ascorbate is widely applied as an antioxidant in pharmaceutical manufacturing, the food industry and in the production of cosmetics.[3] It also acts as a coenzyme and a reducing agent, occurs as a metabolite in some plants and animals and shows in vitro cytotoxic effects in malignant cell lines, of which melanoma cells are particularly susceptible.[4]

In organic synthesis, its most common employment is to induce click chemistry reactions,[5] but it can also be applied in a variety of chemical transformations under different reaction conditions, both as a secondary reactant or as a main reactant. Due to its reducing power, sodium ascorbate is commonly used along with a metallic catalyst for the purpose of reducing it to its most active form, contributing to increased reaction yields. The reducing activity of ascorbate also serves to avoid the formation of undesired byproducts. In addition to conventional metallic catalysts, the ascorbic acid sodium salt can also help to activate photocatalysts, participating in the formation of free radicals to promote photoredox-catalyzed reactions,[6] and plays a role in electrochemical reactions.[7] This graphical review provides a detailed overview of the many applications of sodium l-ascorbate as a reactant in organic chemistry through history.

Figure 1 1,3-Dipolar cycloaddition, part I[5] ^, [8`] [b] [c] [d] [e] [f]

Figure 2 1,3-Dipolar cycloaddition, part II[9`] [b] [c] [d] [e] [f] [g] [h] [i] [j]

Figure 3 1,3-Dipolar cycloaddition, part III[10`] [b] [c] [d] [e] [f] [g] [h] [i]

Figure 4 Substitution of aromatic halides with nitrogen nucleophiles, part I[11`] [b] [c] [d] [e] [f] [g] [h] [i]

Figure 5 Substitution of aromatic halides with nitrogen nucleophiles, part II[12`] [b] [c] [d] [e] [f]

Figure 6 Substitution of aromatic halides with nitrogen nucleophiles, part III[13`] [b] [c] [d] [e]

Figure 7 Reduction reactions, part I[7] ^, [14`] [b] [c]

Figure 8 Reduction reactions, part II[15`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l]

Figure 9 Addition reactions, part I[16`] [b] [c] [d] [e] [f] [g] [h]

Figure 10 Addition reactions, part II[17`] [b] [c] [d] [e] [f]

Figure 11 Addition reactions, part III[6] ^, [18`] [b] [c] [d] [e] [f]

Figure 12 Cross-coupling reactions, part I[19`] [b] [c] [d] [e]

Figure 13 Cross-coupling reactions, part II[20`] [b] [c] [d] [e]

Figure 14 Hydroxylation reactions, part I[21`] [b] [c] [d] [e] [f] [g]

Figure 15 Hydroxylation reactions, part II[22`] [b] [c] [d] [e]

Figure 16 Alkylation reactions, part I[23`] [b] [c] [d]

Figure 17 Alkylation reactions, part II[24`] [b] [c] [d]

Figure 18 Condensation reactions, part I[25`] [b] [c] [d]

Figure 19 Condensation reactions, part II[26`] [b] [c] [d] [e] [f]

Figure 20 Alkyl halide reactions[27`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n]

Figure 21 Formation of heterocycles, part I[28`] [b] [c] [d] [e] [f] [g] [h] [i] [j] [k] [l] [m] [n] [o]

Figure 22 Formation of heterocycles, part II[29a] [b]

Conflict of Interest

The authors declare no conflict of interest.

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Publikationsverlauf

Eingereicht: 16. August 2024

Angenommen nach Revision: 09. Dezember 2024

Artikel online veröffentlicht:
04. März 2025