Visible-light-induced sequential sulfonylation/hydroxylation of allylacetamides leading to β-tert-hydroxy sulfones

Qian, Zhu-Ming; Zuo, Kai-Li; Guan, Zhi; He, Yan‐Hong

doi:10.1016/j.tet.2021.131999

Cited by 6 publications

(2 citation statements)

References 40 publications

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“…[18] A recent study reported the sequential sulfonylation/hydroxylation of allylacetamides, resulting in the formation of β-terthydroxysulfones. [19] This is the only known example in the literature where sulfinic acids are used in conjunction with styrene derivatives under visible light.…”

Section: Introductionmentioning

confidence: 99%

Visible‐Light‐Mediated Synthesis of Bicalutamide by Regioselective Hydroxysulfonylation of Acrylamides

2023

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Synthesis of anticancer drug bicalutamide promoted by visible light in one step from the corresponding N‐arylacrylamide is described. This approach involves a one‐pot hydroxysulfonylation reaction via a photocatalytic redox process. The use of Na2Eosin Y as photocatalyst and blue light allows the access to a broad range of α‐hydroxysulfonylamides bearing a quaternary center in moderate to good yields with complete regioselectivity via radical process.

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Section: Introductionmentioning

confidence: 99%

Visible‐Light‐Mediated Synthesis of Bicalutamide by Regioselective Hydroxysulfonylation of Acrylamides

2023

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“…[18][19][20] Therefore, the synthesis of b-hydroxysulfones has been greatly improved compared to traditional methods. Encouraged by Guan and He's work on visible-light-induced b-hydroxy sulfonylation of sulfinic acids (not compatible with DNA) using eosin Y as an organic photocatalyst, 21 we developed a DELcompatible photooxidation based on commercially available sulfone sources, under mild conditions. This study demonstrates the initial implementation of an on-DNA b-hydroxyl sulfonylation procedure by a photoinduced coupling process using sodium sulfinate or in situ generated ones from ubiquitous sulfonyl chlorides and terminal alkenes.…”

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confidence: 99%

Light-induced β-hydroxy sulfone synthesis in DNA-encoded libraries

Xue,

Yu,

Zhong

et al. 2024

Chem. Commun.

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Photocatalytic Sulfonylation: Innovations and Applications

Huang,

Li,

et al. 2024

Chemistry A European J

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Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due to its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds has drawn significant attention in the pharmaceuticals, agrochemicals, and materials industries due to the unique structure and electronic properties of the sulfonyl groups. Over the past decades, many photocatalytic sulfonylation reactions have been developed. In this review, the recent advances in photocatalyzed sulfonylation have been reviewed since 2020, with a primary focus on discussing reaction design and mechanism.

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Visible-light-induced sequential sulfonylation/hydroxylation of allylacetamides leading to β-tert-hydroxy sulfones

Cited by 6 publications

References 40 publications

Visible‐Light‐Mediated Synthesis of Bicalutamide by Regioselective Hydroxysulfonylation of Acrylamides

Visible‐Light‐Mediated Synthesis of Bicalutamide by Regioselective Hydroxysulfonylation of Acrylamides

Light-induced β-hydroxy sulfone synthesis in DNA-encoded libraries

Photocatalytic Sulfonylation: Innovations and Applications

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