Oxidation of Thiols with IBX or DMP: One-pot Access to Thiosulfonates or 2-Iodobenzoates and Applications in Functional Group Transformations

10 February 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Thiosulfonates are accessed by oxidation of feed-stock thiols using either DMP in DCM or IBX in MeCN at rt (~30 degree C). The protocol gives access to a variety of thiosulfonates in good to excellent yields from both aromatic and aliphatic thiols. The reaction with DMP is found to be better than IBX in terms of reaction rate and conversion, whereas the oxidation with DMP requires lower equivalent than IBX. Benzyl thiols are however found to follow a different reaction pathway when treated with DMP; O-benzyl esters of o-iodobenzoates were isolated. The 1H NMR spectroscopic monitoring studies for the IBX-mediated oxidation of thiol found disulfide as an initial intermediate, which is proposed to undergoes a cascade of oxidations to produce thiosulfonate

Keywords

Hypervalent Iodanes
Thiols
Oxidation
2-Iodobenzoate
Thiosulfonates

Supplementary materials

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Title
Oxidation of Thiols with IBX or DMP: One-pot Access to Thiosulfonates or 2-Iodobenzoates and Applications in Functional Group Transformations
Description
This is a very good selective oxidative transformation of thiols to thiosulfonates and benzyl benzoates. To the best of our knowledge, this is the first report that offers the direct challenging transformation of benzyl thiols to corresponding esters, alcohols and aldehydes through a tandem process. Herein, we have used hypervalent iodanes (DMP, IBX, and IBA) which are considered as a mild oxidizing reagent with eco-friendly attributes.
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