Catalyst-Free C(sp²)-H Borylation through Aryl Radical Generation from Thiophenium Salts via Electron Donor–Acceptor Complex Formation

Organic Letters, Год журнала: 2022, Номер 24(40), С. 7434 - 7439

Опубликована: Окт. 3, 2022

Aryl borates lie at the heart of carbon–carbon bond couplings, and they are widely applied to synthesis functional materials, pharmaceutical compounds, natural products. Currently, synthetic methods for aryl mostly limited metal-catalyzed routes, nonmetallic strategies remain comparatively underdeveloped. Herein, we report a mild, scalable, visible-light-induced cross-coupling between dibenzothiophenium triflate salts bis(catecholato)-diboron construction C–B bonds in absence base, transition metal–ligand complex, or photoredox catalyst. Mechanistic studies reveal that this transformation is achieved through an electron donor–acceptor (EDA) complex activation The mild reaction conditions allow preparation aromatic good yields with excellent group tolerance. This photochemical protocol was also successfully late-stage modification products drug intermediate, greatly demonstrating broadened utility.

Язык: Английский

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Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions

Chemical Science, Год журнала: 2023, Номер 14(16), С. 4278 - 4287

Опубликована: Янв. 1, 2023

Boronic acids as a tunable hydroxy source display unique reactivity paradigm through hitherto unknown aryne-induced multicomponent reactions.

Язык: Английский

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Organohypervalent heterocycles

Chemical Society Reviews, Год журнала: 2024, Номер 53(9), С. 4786 - 4827

Опубликована: Янв. 1, 2024

This review summarizes structural and synthetic aspects of heterocyclic molecules incorporating an atom a hypervalent main-group element. The higher thermal stability heterocycles, as compared to their acyclic analogs, adds special feature chemistry.

Язык: Английский

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Hydrodeuteroalkylation of Unactivated Olefins Using Thianthrenium Salts

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(36)

Опубликована: Июнь 13, 2024

Isotopically labeled alkanes play a crucial role in organic and pharmaceutical chemistry. While some deuterated methylating agents are readily available, the limited accessibility of other deuteroalkyl reagents has hindered synthesis corresponding products. In this study, we introduce nickel-catalyzed system that facilitates various deuterium-labeled through hydrodeuteroalkylation d2-labeled alkyl TT salts with unactivated alkenes. Diverging from traditional reagents, thianthrenium (TT) can effectively selectively deuterium at α position chains using D

Язык: Английский

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Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Язык: Английский

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