Recent Progress in the Construction of S—S, P—S and C—S Bonds Involving O2-Initiated Sulfur-Centered Radicals

doi:10.6023/cjoc202105015

Abstract

Sulfur-containing organic compounds have been widely used in organic synthesis, pharmaceuticals, pesticides and functional materials. Thus, the development of green, mild and highly efficient methodologies for the synthesis of organosulfur compounds is of great importance. Some sulfur-containing compounds can be directly initiated by O₂ as the ideal green oxidant to generate sulfur-centered radicals, and the corresponding radical reactions provide a novel approach to the construction of S—S, P—S and C—S bonds. These reactions can be performed under mild conditions without the use of toxic reagents, transition metals and strong oxidants. In this review, the recent progress in the construction of S—S, P—S and C—S bonds involving O₂-initiated sulfur-centered radicals is introduced on the basis of different reaction types.

Key words: oxygen, sulfur-centered radicals, organosulfur compounds, radical reactions

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Xi Zhao, Yingcong Ou, Yan Liu, Keiji Maruoka, Qian Chen. Recent Progress in the Construction of S—S, P—S and C—S Bonds Involving O₂-Initiated Sulfur-Centered Radicals[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3366-3378.

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Fig. & Tab. 37

Scheme 1. Reactions of O2-initiated thiyl radicals

Scheme 2. Air oxidation of thiols under sonication

Scheme 3. Bio-based green solvent mediated disulfide synthesis

Scheme 4. Base-catalyzed cross-dehydrogenative coupling of thiols under air

Scheme 5. Cs2CO3-catalyzed aerobic oxidative cross-dehydro- genative coupling of P(O)H compounds with thiols

Scheme 6. K2CO3-promoted aerobic oxidative cross-coupling of trialkyl phosphites with thiophenols

Scheme 7. Ionic liquid-catalyzed difunctionalization of alkenes under oxygen

Scheme 8. Controlled synthesis of β-hydroxy sulfides and β- hydroxy sulfoxides

Scheme 9. Difunctionalization of alkenes under air

Scheme 10. Difunctionalization of alkenes under O2

Scheme 11. Direct synthesis of β-keto sulfides via reactions of alkenyl halides with thiophenols under air

Scheme 12. Direct synthesis of β-keto sulfides via reactions of vinyl phosphates with thiophenols under O2

Scheme 13. Cyclization of 2-aminobenzenethiols with α,β-unsaturated ketones under air

Scheme 14. Air-induced bis-sulfenylation of alkenes

Scheme 15. Visible-light-initiated oxidative coupling of aryldiazo sulfones with thiols under air

Scheme 16. Hydrothiolation of alkenes and alkynes catalyzed by thiazolium salts

Scheme 17. Hydrothiolation and difunctionalization of alkenes under air

Scheme 18. Oxygen-triggered cyclization of thiophenols and alkynes

Scheme 19. Thiyl radical cascade reaction of aryl alkynoates

Scheme 20. Direct synthesis of β-hydroxysulfones via reactions of alkenes with arylsulfinic acids under air

Scheme 21. Difunctionalization of terminal alkynes under air

Scheme 22. Direct synthesis of β-keto sulfones via reactions of alkenes with arylsulfinic acids under air

Scheme 23. Direct synthesis of β-keto sulfones via reactions of vinyl phosphates with arylsulfinic acids under O2

Scheme 24. Iron-catalyzed difunctionalization of alkenes under air

Scheme 25. Difunctionalization of alkenes with arylsulfinic acids and NBS under air

Scheme 26. Difunctionalization of alkenes with sulfonyl hydrazides under O2

Scheme 27. Cu-catalyzed oxidative coupling of alkenes with thiols under air

Scheme 28. O2-induced thiocyanation of styrenes

Scheme 29. Cyclization of cyclohexanones and 2-aminobenzenethiols

Scheme 30. Sulfenylation of C(sp3)—H bonds of pyrazolones under air

Scheme 31. Radical cyclization of 2?aminobenzenethiols and ketones under air

Scheme 32. Sulfenylation of C(sp3)—H bonds of 1,3-dicarbonyl compounds under air

Scheme 33. Sulfenylation and C—C bond cleavage of 3-oxobutyric amides/esters under O2

Scheme 34. α-Disulfenylation and C—C bond cleavage of 3- oxobutyric amides under O2

Scheme 35. Methylene insertion into disulfide bonds under air

Scheme 36. Iron-catalyzed α-sulfenylation of ketones under air

Scheme 37. Direct C(sp3)—H sulfenylation of xanthene derivatives under air

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氧气引发的硫中心自由基参与的构建S—S、P—S和C—S键研究进展

Recent Progress in the Construction of S—S, P—S and C—S Bonds Involving O₂-Initiated Sulfur-Centered Radicals

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