Light-promoted metal-free cross dehydrogenative couplings on ethers mediated by NFSI: reactivity and mechanistic studies
作者:Redouane Beniazza、Baptiste Abadie、Lionel Remisse、Damien Jardel、Dominique Lastécouères、Jean-Marc Vincent
DOI:10.1039/c7cc05854c
日期:——
Cross dehydrogenative couplings on ethers occur very effectively using N-fluorobis(phenyl)sulfonimide (NFSI) as oxidizing agent under UVA irradiation in the presence of 2 mol% benzophenone. The reaction was shown to proceed first by fast radical fluorination of the α-C–H bond of ethers, followed by HF elimination to yield the highly electrophilic oxocarbenium ion as a key intermediate.
在2摩尔%二苯甲酮的存在下,使用N-氟双(苯基)磺酰亚胺(NFSI)作为氧化剂,在UVA照射下,醚上的交叉脱氢偶联反应非常有效。该反应首先通过醚的α-C–H键的快速自由基氟化反应进行,然后通过HF消除反应生成高度亲电的氧碳鎓离子作为关键中间体。