Photoredox/copper-catalyzed coupling of terminal alkynes with P(O)SH compounds leading to alkynyl phosphorothioates

Zheng, Zhuo; He, Jiali; Ma, Qianru; Zhang, Yumeng; Liu, Yan; Tang, Guo; Zhao, Yufen

doi:10.1039/d2gc00816e

Cited by 22 publications

(4 citation statements)

References 32 publications

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“…Subsequently, the same group [42] reported a novel photoredox/copper‐catalyzed dehydrogenation coupling of terminal alkynes 70 with ( i PrO) 2 P(O)SH for the direct synthesis of S ‐alkynyl phosphorothioates 71 with moderate to good yields (Scheme 28). A series of alkyl‐ and aryl‐substituted terminal alkynes can be applied to this transformation, especially some terminal alkynes containing pharmacologically active skeletons (such as naproxen, losoprofen, ibuprofen, and steroid acid derivatives) can be also successfully transformed to obtain corresponding products.…”

Section: Photo‐induced Radical Transformation To Construct Sulfur‐con...mentioning

confidence: 99%

Recent Advances in the Direct Synthesis of Sulfur‐Containing Organophosphorus Compounds via Radical Processes

et al. 2023

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Phosphonothioates, phosphinothioates and phosphorothioates are regarded as an important class of sulfur‐containing organophosphorus compounds. Because of the unique P(O)S−R group, these compounds have important biological activities and thus have been widely used in the fields of pharmaceuticals and pesticides. In recent years, the development of sulfur‐containing organophosphorus compounds by radical processes has attracted considerable attention in organophosphorus chemistry. Along these lines, in this review, the recent advances in the synthesis of sulfur‐containing organophosphorus compounds were systematically summarized. According to the different ways of generating radicals during the formation process of phosphonothioates, phosphinothioates and phosphorothioates, these transformations can be divided into four categories: (1) Oxidant or metal‐free promoted radical transformation to fabricate sulfur‐containing organophosphorus compounds; (2) Copper‐catalyzed radical transformation to produce sulfur‐containing organophosphorus compounds; (3) Photo‐induced radical transformation to prepare sulfur‐containing organophosphorus compounds; (4) Electro‐induced radical transformation to derive sulfur‐containing organophosphorus compounds.

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Section: Photo‐induced Radical Transformation To Construct Sulfur‐con...mentioning

confidence: 99%

Recent Advances in the Direct Synthesis of Sulfur‐Containing Organophosphorus Compounds via Radical Processes

et al. 2023

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“…Generally, methods for the synthesis of organophosphorothioates mainly rely on the formation of the P–S or C–S bonds through substitution reactions, cross-coupling reactions, and radical-based reactions . In recent years, Ir or Cu catalysts showed their uniqueness in chemical bond activation and were proven to be successful for realizing various challenging chemical reactions .…”

Section: Introductionmentioning

confidence: 99%

Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation

Zhang,

Li,

Yang

et al. 2024

J. Org. Chem.

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A photoredox/copper-catalyzed cascade radical cyclization/phosphorothiolation reaction of N-allylbromoacetamides and P(O)SH compounds has been established. A broad range of novel nonfluorine-or difluoro-substituted 2-pyrrolidinones bearing the C(sp 3 )-SP(O)(OR) 2 moiety can be conveniently constructed in moderate to good yields under mild conditions. Importantly, most of the tested phosphorothiolated 2-pyrrolidinones showed potent inhibitory effects toward both AChE and BChE.

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“…When it comes to the S -alkynylation of phosphorothioate diesters, Tang has recently reported an elegant approach through a dual photoredox/copper catalysis under operationally simple conditions. 11 However, to the best of our knowledge there are currently still no procedures reported for the S -dienylation of phosphorotioate diesters. Considering the intriguing potential biological attributes inherent in these novel organophosphorous compounds, it is highly desirable to develop general, sustainable and simple procedures for their synthesis.…”

Section: Introductionmentioning

confidence: 99%

Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides

Piedra,

Gebler,

Valdés

et al. 2023

Chem. Sci.

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Photoredox/copper-catalyzed coupling of terminal alkynes with P(O)SH compounds leading to alkynyl phosphorothioates

Abstract: The direct construction of C(sp)-S-P(O) moiety from unactivated terminal alkynes has been an unbroken research field for a long time. Alkynyl phosphorothioates are obtained by coupling terminal alkynes and P(O)SH....

Cited by 22 publications

References 32 publications

Recent Advances in the Direct Synthesis of Sulfur‐Containing Organophosphorus Compounds via Radical Processes

Recent Advances in the Direct Synthesis of Sulfur‐Containing Organophosphorus Compounds via Radical Processes

Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation

Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides

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