期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 39, 页码 12945-12949出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807941
关键词
amines; halogenation; photochemistry; radicals; reaction mechanisms
资金
- Leverhulme Trust [RPG-2016-131]
- EPSRC [EP/P004997/1]
- European Research Council [758427]
- AstraZeneca
- Deanship of Scientific Research, King Faisal University
- EPSRC [EP/P004997/1, 1735824] Funding Source: UKRI
The selective functionalization of C(sp(3))-H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5-H-atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late-stage functionalization of amino acids and a dipeptide.
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