Photochemical Halogen-Bonding Promoted Synthesis of Vinyl Sulfones via Vinyl and Sulfonyl Radicals

Organic Letters, Год журнала: 2024, Номер 26(3), С. 636 - 641

Опубликована: Янв. 10, 2024

A photochemical halogen-bonding-assisted synthesis of vinyl sulfones via radical–radical cross-coupling bromines and sodium sulfinates is developed. This methodology offers a facile efficient approach to various with excellent functional group tolerance under metal-, photocatalyst-, base-, oxidant-free conditions. The reaction also applicable for the late-stage functionalization drug molecules hectogram scale. Moreover, instead sulfites being prepared, these reactions could be conducted using sulfonyl chlorides in one-pot method.

Язык: Английский

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From molecules to medicine: thiol selective bioconjugation in synthesis of diagnostic and therapeutic radiopharmaceuticals

Theranostics, Год журнала: 2024, Номер 14(6), С. 2396 - 2426

Опубликована: Янв. 1, 2024

Radiolabeling of biomolecules and cells with radiolabeled prosthetic groups has significant implications for nuclear medicine, imaging, radiotherapy.Achieving site-specific controlled incorporation prostheses under mild reaction conditions is crucial minimizing the impact on bioactivity compounds.The targeting natural abundant amino acids during radiolabeling often results in nonspecific uncontrolled modifications.Cysteine distinguished by its low abundance unique nucleophilicity.It therefore an optimal target site-selective parameters.This review extensively discusses thiol-specific provides a critical analysis comprehensive study synthesis these groups, their vitro vivo stability profiles, kinetics, resulting adducts, overall ability biomolecules.The insights presented here aim to facilitate development highly efficient radiopharmaceuticals, initially preclinical settings ultimately clinical applications.

Язык: Английский

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Synthesis of (E)‐β‐Iodovinyl Sulfones via HI‐mediated Vicinal Iodosulfonylation of Alkynes with Sodium Sulfinates

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(6)

Опубликована: Март 21, 2024

Abstract Hydroiodic acid‐mediated vicinal iodosulfonylation reaction of alkynes with sodium sulfinates is proposed for the synthesis ( E )‐ β ‐iodovinyl sulfones. The method easy to operate, environmentally friendly, using inexpensive and easily available raw materials, giving target products good regio‐ stereoselectivity in satisfactory yields.

Язык: Английский

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Visible-Light-Induced Synthesis of Vinyl Sulfones via Decarboxylative Sulfonylation of Cinnamic Acids Using Sulfonylazides/p-Toluenesulfonylmethyl Isocyanide/β-Keto Sulfones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10919 - 10928

Опубликована: Июль 16, 2024

An efficient visible-light-induced synthesis of vinyl sulfones has been accomplished via decarboxylative sulfonylation cinnamic acids using sulfonylazides,

Язык: Английский

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Synthesis of polysubstituted vinyl sulfones by direct C‐S cross‐coupling

Chemistry - A European Journal, Год журнала: 2024, Номер 31(8)

Опубликована: Ноя. 22, 2024

Vinyl sulfones are valued for their unique chemical properties and bioactivity, but creating a wide range of different analogs remains challenge. To address this limitation, we have developed novel approach that facilitates the synthesis polysubstituted vinyl sulfones. This method utilizes dual functionality NIS as promoter enables sulfonation elimination in We used broad applicability, efficiency, selectivity, functional group tolerance to synthesize more than 70 examples. Additionally, competition experiments provided insights into reactivity selectivity transient sulfonyl radical towards various C-C multiple bonds. Herein, describe using mild protocol late-stage complex molecules simplify specific targets enable modification natural products advanced materials.

Язык: Английский

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Photoredox-Catalyzed Multicomponent α-Sulfonylation of Terminal Alkynes

Organic Letters, Год журнала: 2024, Номер 26(46), С. 9978 - 9983

Опубликована: Ноя. 11, 2024

A generality-oriented and adaptive α-sulfonylation of alkynes via photoinduced multicomponent radical cross-coupling terminal with sulfinates a variety alcohols, thiophenols, or selenophenols has been explored. This protocol features mild conditions, good functional group tolerability, broad substrate scope, excellent chemo-, site-, stereoselectivity, applicability to late-stage functionalization. It provides modular platform for the synthesis value-added structurally diverse α-sulfonyl-containing multisubstituted alkenes from simple precursors.

Язык: Английский

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Visible-light-induced hydrosulfonylation of alkynes driven by electron-donor–acceptor (EDA) complexes

Tetrahedron Letters, Год журнала: 2024, Номер 153, С. 155368 - 155368

Опубликована: Ноя. 16, 2024

Язык: Английский

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