Halogen Atom Transfer-Induced Homolysis of C-F Bonds by the Excited-State Boryl Radical

被引:14
|
作者
Koo, Jangwoo [1 ]
Kim, Weonjeong [1 ]
Jhun, Byung Hak [2 ]
Park, Subin [1 ]
Song, Dayoon [2 ]
You, Youngmin [2 ]
Lee, Hong Geun [1 ]
机构
[1] Seoul Natl Univ, Coll Nat Sci, Dept Chem, Seoul 08826, South Korea
[2] Yonsei Univ, Dept Chem & Biomol Engn, Seoul 03722, South Korea
基金
新加坡国家研究基金会;
关键词
N-HETEROCYCLIC CARBENES; SODIUM-BOROHYDRIDE; BORANE COMPLEXES; LEWIS-BASES; GENERATION; REACTIVITY; ACTIVATION; CATALYSIS; FLUORINE; ALKENES;
D O I
10.1021/jacs.4c06337
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel reactivity toward C-F bond functionalization has been developed, which could be designated as fluorine atom transfer (FAT). A photoexcited state of an N-heterocyclic carbene-ligated boryl radical exhibits a transcendent reactivity, capable of activating chemically inert carbon-fluorine bonds through homolysis. Combined experimental and computational studies suggest that the ligated boryl radical species directly abstracts a fluorine atom from the organofluoride substrates to provide valuable carbon-centered radicals.
引用
收藏
页码:22874 / 22880
页数:7
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