Liu Tao, Mei Tian-Sheng, Yu Jin-Quan
†Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
J Am Chem Soc. 2015 May 13;137(18):5871-4. doi: 10.1021/jacs.5b02065. Epub 2015 Apr 30.
Aliphatic amides are selectively functionalized at the γ- and δ-positions through directed radical 1,5 and 1,6 H-abstractions, respectively. The initially formed γ- or δ-lactams are intercepted by N-iodosuccinimide and trimethylsilyl azide, leading to double and triple C-H functionalizations at the γ-, δ-, and ε-positions. This new reactivity is exploited to convert alkyls into amino alcohols and allylic amines.
脂肪族酰胺分别通过定向自由基1,5-和1,6-H-抽象在γ-和δ-位进行选择性官能化。最初形成的γ-或δ-内酰胺被N-碘代琥珀酰亚胺和三甲基硅基叠氮化物截获,导致在γ-、δ-和ε-位进行双C-H官能化和三C-H官能化。利用这种新的反应性将烷基转化为氨基醇和烯丙基胺。