Radical Fluorosulfonyl Arylation of Alkenes: Accessing FSO₂-Functionalized Chromanes via Formal Endo and Exo Cyclization

Organic Letters, Год журнала: 2022, Номер 24(44), С. 8170 - 8175

Опубликована: Окт. 31, 2022

The introduction of sulfonyl fluoride groups into bioactive molecules can often bring about enhanced biological activity, which has attracted more research interest in chemical biology and drug development recent years. Here, we report the a radical fluorosulfonylation alkenes/intramolecular arylation cascade for construction chromanes with attached. 1,2-fluorosulfonyl reactions proceed well both endo exo cyclization fashions, allowing further variation distance between chromane core group.

Язык: Английский

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C(sp³)–H fluorosulfonylvinylation/aza-Michael addition approach to FSO₂-functionalized tetrahydropyridines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3805 - 3810

Опубликована: Янв. 1, 2023

We have developed an efficient approach for the synthesis of FSO 2 -functionalized tetrahydropyridines from propargyl alcohols, Cl, and anilines.

Язык: Английский

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Generation of Aromatic N‐Heterocyclic Radicals for Functionalization of Unactivated Alkenes

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(52)

Опубликована: Ноя. 10, 2023

Nitrogen-centered radicals (NCRs) have been widely recognized as versatile synthetic intermediates for the construction of nitrogen containing molecules high value. As such, there has a long-standing interest in field organic synthesis to develop novel nitrogen-based and explore their inherent reactivity. In this study, we present generation aromatic N-heterocyclic application diverse functionalization unactivated alkenes. Bench-stable pyridinium salts were employed crucial NCR precursors, which enabled efficient conversion various alkenes into medicinally relevant alkylated amines. This approach offers an unexplored retrosynthetic disconnection related that commonly possess therapeutic Furthermore, platform can be extended densely functionalized heterocyclic amines by utilizing disulfides diethyl bromomalonate radical quenchers. Mechanistic investigations indicate energy transfer (EnT) pathway involving formation transient radical, addition alkenes, subsequent amination product through either hydrogen atom (HAT) or processes.

Язык: Английский

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Radical Fluorosulfonamidation: A Facile Access to Sulfamoyl Fluorides

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(34)

Опубликована: Июнь 4, 2024

Recently, the introduction of fluorosulfonyl (-SO

Язык: Английский

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Advances in sulfur fluoride exchange for chemical biology

Trends in Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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