An efficient one-pot sequential hydrogen isotope exchange (HIE)/ reductive deuteration approach was developed for the preparation of α,β-deuterated alcohols using ketones as the precursors. The HIE step can also be used for the synthesis of α-deuterated ketones. This method has been applied in the synthesis of four deuterated drug and MS internal standards.Letter pubs.acs.org/OrgLett

A highly chemoselective reductive deuteration of acyl fluorides to provide α,α-dideuterio alcohols with exquisite levels of deuterium incorporation was developped using SmI2 and D2O as deuterium source. This method introduces...

We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazole using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher...

Deuterated polymers have wild applications but limited synthetic methods. In this study, we report an efficient two-step approach for the synthesis of deuterated polyesters and polyurethanes. Firstly, two practical single electron transfer (SET) reductive deuteration methods have been developed for site-selective introduction of C(sp3)–D into diol monomers. 9 deuterated diol monomers with high deuterium incorporations were synthesized under SmI2-D2O and/or Na-EtOD-d 1 SET reductive deuteration conditions. Then, 6 typical deuterated polyesters and polyurethanes were synthesized using those deuterated monomers under typical polymerization conditions. In all the synthesized polymers, high deuterium incorporation was fully maintained, which showcased the potential application of this approach for the synthesis of polymers with site-specific deuterium labelling.

The dynamic disulfide linkage plays a vital role in various biological processes as well as drugs and biomaterials. Oxidation of thiols is a widely utilized approach for disulfide synthesis; however, achieving both optimal reactivity and selectivity continues to pose a significant challenge. Here, we report the redox-click chemistry for disulfide formation from thiols by sulfonyl fluorides in both batch and flow-mode. Sulfuryl fluoride is a potent oxidant with exceptional selectivity toward thiols. This reaction's unique characteristics satisfy click chemistry's stringent criteria with its high thermodynamic driving force, simple reaction conditions, wide scope, quantitative yields, exceptional chemoselectivity, and non-chromatographic purification process. Furthermore, the redox click chemistry's ability to joining various modular thiol units was showcased in the synthesis of symmetrical, unsymmetrical and cyclic disulfides, poly(disulfide)s, and the in vivo disulfide cross-linked biomedical hydrogels.