36611-88-8Relevant academic research and scientific papers
Decatungstate-Catalyzed C(sp3)-H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality
Bissonnette, Noah B.,Macmillan, David W. C.,Sarver, Patrick J.
, p. 9737 - 9743 (2021/07/19)
Here we report the direct conversion of strong, aliphatic C(sp3)-H bonds into the corresponding alkyl sulfinic acids via decatungstate photocatalysis. This transformation has been applied to a diverse range of C(sp3)-rich scaffolds, including natural products and approved pharmaceuticals, providing efficient access to complex sulfur-containing products. To demonstrate the broad potential of this methodology for the divergent synthesis of pharmaceutically relevant molecules, procedures for the diversification of the sulfinic acid products into a range of medicinally relevant functional groups have been developed.
Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions
Day, Jacob J.,Neill, Deshka L.,Xu, Shi,Xian, Ming
supporting information, p. 3819 - 3822 (2017/07/26)
Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.
Photoextrusion of SO2 from Arylmethyl Sulfones: Exploration of the Mechanism by Chemical Trapping, Chiral, and CIDNP Probes
Givens, Richard S.,Hrinczenko, Borys,Liu, Jerry H.-S.,Matuszewski, Bogdan,Tholen-Collison, Joan
, p. 1779 - 1789 (2007/10/02)
The photochemistry of eight benzylic sulfones, all of which efficiently extrude sulfur dioxide, was studied by a variety of methods.Optically active sulfones (S)-(-)-8, (S)-(-)-11, (S)-(-)-12, (S)-(+)-13, and (R)-(+)-14 were employed to measure the extent of the "hidden" return of the initial photogenerated intermediates by the stereoequilibration of the chiral center.By comparison of the regioisomeric methyl sulfones 11 vs. 13 and 12 vs. 14, preferential C-S bond fragmentation on the naphthyl side was established for the singlet excited sulfones.Added nucleophilic and proton trapping agents had no effect on the course of the reaction, ruling out ionic intermediates.The three hydrocarbon products of photodesulfonation from the unsymmetrical sulfones 8-14 provided a measure of the cage effects, which were highly structure and multiplicity dependent.Rate constants for reaction, and fluorescence, as well as the energy transfer rates from benzophenone were determined.The reaction rate constant for singlet reactivity from the 1-naphthyl sulfones was about three times greater than that for the 2-naphthyl derivatives.CIDNP studies showed a strong product signal for the 1-naphthyl sulfones from desulfonation of a triplet caged radical pair.Naphthaldehyde formation, a very minor, triplet process, was also detected by the CIDNP study of sulfones 9-12.
A CONVENIENT AND GENERAL SYNTHESIS OF ALKANE SULFINIC ACIDS
Ueno, Yoshio,Kojima, Akihiko,Okawara, Makoto
, p. 2125 - 2128 (2007/10/02)
2-(Alkylsulfonyl)benzothiazoles are reduced with sodium tetrahydroborate to give alkane sulfinic acids in good yield.
