Direct C2-H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes

被引：5
作者：
Mamone, Martina [1 ]
Gentile, Giuseppe [1 ]
Dosso, Jacopo [1 ]
Prato, Maurizio [1 ,2 ,3 ]
Filippini, Giacomo [1 ]
机构：
[1] Univ Trieste, Dept Chem & Pharmaceut Sci, INSTM UdR Trieste, Via Licio Giorgieri 1, I-34127 Trieste, Italy
[2] Basque Res & Technol Alliance BRTA, Ctr Cooperat Res Biomat CIC BiomaGUNE, Paseo Miramon 194, Donostia San Sebastian 20014, Spain
[3] Basque Fdn Sci, Ikerbasque, Bilbao 48013, Spain
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷
关键词：
alkylation; EDA complex; halogens; indoles; photochemistry; DONOR-ACCEPTOR COMPLEX; LIGHT-IRRADIATION; ELECTRON; FUNCTIONALIZATION;
D O I：
10.3762/bjoc.19.42
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A light-driven metal-free protocol for the synthesis of sulfone-containing indoles under mild conditions is reported. Specifically, the process is driven by the photochemical activity of halogen-bonded complexes formed upon complexation of a sacrificial donor, namely 1,4-diazabicyclo[2.2.2]octane (DABCO), with alpha-iodosulfones. The reaction provides a variety of densely functionalized products in good yields (up to 96% yield). Mechanistic investigations are reported. These studies provide convincing evidences for the photochemical formation of reactive open-shell species.
引用
收藏
页码：575 / 581
页数：7
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