Synfacts, Год журнала: 2024, Номер 20(05), С. 0534 - 0534
Опубликована: Апрель 15, 2024
Key words arylboronate esters - reductive coupling nickel catalysis Suzuki
Язык: Английский
Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Март 7, 2025
Comprehensive Summary Cross‐coupling reactions between aryl halides and thiolates or selenolates typically require transition metals, photocatalysts, strong bases, or/and malodorous thiols/selenols, with various mechanisms proposed. This study aims to leverage a new application of neutral ChB address these challenges enable very simple photoinduced cross‐electrophile C—S/Se coupling using readily available chalcogen electrophiles. Mechanistic investigations have revealed the important role in facilitating single electron transfer processes, thereby enabling generation thiolates/selenolates from stable electrophiles α ‐aminoalkyl radicals, which possess capability abstract halogen atoms iodides. Moreover, provided support for radical nucleophilic substitution mechanism.
Язык: Английский
Процитировано
1
ACS Catalysis, Год журнала: 2024, Номер 14(13), С. 9985 - 9992
Опубликована: Июнь 19, 2024
The regio- and stereoselective hydroarylation of internal alkynes via transition-metal catalysis offers a direct approach for designing highly stereodefined multifunctionalized olefins. Through recognition electronic bias, β-syn-hydroarylation poor with arylboronic acids has been well studied. However, from the same starting materials, achieving opposite α-selective anti-stereoselective remains significant challenge due to these inherent biases. Therefore, an alternative synthetic pathway trisubstituted alkenes reversed positioning configuration substituents is desirable. Based on steric repulsion-induced regioselectivity transient post-addition coordination-directed stereoselectivity, we report herein α-hydroarylation method phenylpropiolic esters using nickel catalyst that promotes formal anti-addition pathway. A broad range organoboronic acid derivatives are compatible this protocol, offering selectivity traditional reactions. distinct advantages our include precise control over selectivity, reduced loading, tolerance toward functional groups. These features highlight potential in synthesis late-stage modification alkyne-based drug intermediates, showcasing its versatility applicability organic synthesis.
Язык: Английский
Процитировано
3
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Май 4, 2025
Aryl borates are one of the most important synthetic materials in organic synthesis. Herein, we report a visible-light-induced electron donor-acceptor (EDA)-based borylation protocol between thianthrenium salts and 1,4-diazabicyclo[2.2.2]octane (DABCO) for synthesis various aryl boronates without photocatalyst or stepwise processing. Remarkably, this photochemical strategy is compatible with wide range sensitive functional groups affords excellent yields. Moreover, quantitative recovery thianthrene feedstock lowers reaction cost.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2024, Номер unknown
Опубликована: Сен. 18, 2024
Herein, we reported a copper(0)-catalyzed reductive coupling of disulfurating reagents and (hetero)aryl/alkyl halides. Copper(0) can be directly inserted into tetrasulfide then undergoes with (hetero)aryl Iodides to construct disulfide. The method features the unprecedented use (tetrasulfides) in cross-coupling chemistry is convenient broad substrate scopes, even applicable different halogenated hydrocarbons. It worth noting that methodology practical late-stage modification bioactive scaffolds pharmaceuticals. In meantime, synthesis disulfides successfully achieved on gram scale, indicating approach highly valuable.
Язык: Английский
Процитировано
1
Synfacts, Год журнала: 2024, Номер 20(05), С. 0534 - 0534
Опубликована: Апрель 15, 2024
Key words arylboronate esters - reductive coupling nickel catalysis Suzuki
Язык: Английский
Процитировано
0