Base-Promoted Homolytic Aromatic Substitution (BHAS) Reactions and Hydrodehalogenations Driven by Green Light and an Iron(III)-NHC Photoredox Catalyst.

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Tác giả: Lisa H M de Groot, Valtýr Freyr Hlynsson, Clara García-Mateos, Catherine E Johnson, Reiner Lomoth, Alpesh K Sharma, Kenneth Wärnmark

Ngôn ngữ: eng

Ký hiệu phân loại:

Thông tin xuất bản: Germany : Chemistry (Weinheim an der Bergstrasse, Germany) , 2025

Mô tả vật lý:

Bộ sưu tập: NCBI

ID: 691645

An Fe(III)-NHC complex has been employed for the green light driven catalysis of base-promoted homolytic aromatic substitution (BHAS) reactions. Tributylamine was used as a sacrificial electron donor, together with potassium carbonate as base in dimethyl sulfoxide as solvent. In contrast to previously studied photocatalysts, the excited Fe(III)-NHC complex is not reducing the arylhalide substrates. Instead, the latter are activated by α-aminoalkyl radicals formed upon reductive quenching of the photocatalyst by tributylamine. Avoiding strongly reducing photocatalysts as well as strong base, these mild reaction conditions allowed for the expansion of the substrate scope to accommodate also aldehyde and ester substituents. 100 % conversion was obtained after 48 h of irradiation. In this way a wide variety of cyclized products and their corresponding hydrodehalogenated products were obtained as isolated and pure compounds, in the vast majority of cases.
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