Rongalite, Sodium hydroxymethanesulfinate

Product Manager

Sandra Forbes

Rongalite generates in situ sulfite anions. Hence, sodium hydroxymethanesulfinate can serve both as a reducing agent and as a reagent for sulfone synthesis.

Recent Literature

Utilizing cost-effective rongalite as a reducing agent facilitates a transition metal- and hydride-free chemoselective reduction of α-keto esters and α-keto amides through a radical-based mechanism, yielding a broad spectrum of α-hydroxy esters and α-hydroxy amides with excellent productivity. This gentle and chemoselective approach is well-suited for use alongside other reducible functional groups, including halides, alkenes, amides, and nitriles.

S. Golla, H. P. Kokatla, J. Org. Chem., 2022, 87, 9915-9925.

DOI: 10.1021/acs.joc.2c00936

Employing low-cost rongalite as a reducing agent allows for a transition metal- and hydride-free chemoselective reduction of α-keto esters and α-keto amides through a radical pathway, resulting in the production of a diverse array of α-hydroxy esters and α-hydroxy amides with remarkably high yields. This gentle yet chemoselective method is amenable to the presence of other reducible functional groups, including halides, alkenes, amides, and nitriles.

S. Golla, H. P. Kokatla, J. Org. Chem., 2022, 87, 9915-9925.

DOI: 10.1021/acs.joc.2c00936

Rongalite facilitates a seamless, one-pot synthesis of aryl alkyl sulfides from disulfides and alkyl halides at ambient temperature. This protocol operates without the need for metals or strong bases, providing mild reaction conditions, straightforward operational procedures, short reaction durations, and high product yields.

R.-y. Tang, P. Zhong, Q.-l. Lin, Synthesis, 2007, 85-91.

DOI: 10.1055/s-2006-950363

An innovative [1+1+1+1+1+1] annulation strategy enables the synthesis of β,β-dithioketones through the concurrent cleavage of C-C and C-S bonds. In this transformation, rongalite functions as a C1 building block, a sulfur(II) synthon, and a reducing agent. This step-efficient approach facilitates the challenging assembly of C5-substituted 1,3-dithianes under mild and straightforward reaction conditions.

D.-S. Yang, X.-L. Chen, C.-Y. Wu, B.-C. Tang, Y.-C. Xiao, Y.-D. Wu, A.-X. Wu, Org. Lett., 2024, 26, 4340-4345.

DOI: 10.1021/acs.orglett.4c01364

Quoted from:

https://www.organic-chemistry.org/chemicals/reductions/rongalite-sodiumhydroxymethanesulfinate.shtm

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