Base-Free Selective O-Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles
Base-Free Selective O-Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles
复制标题
偕胺肟与二芳基碘鎓盐的无碱选择性 O-芳基化和顺序 [3,3]-重排：2-取代苯并恶唑的合成
DOI：
10.1002/adsc.201700906
复制
发表时间：
2017
影响因子：
5.4
通讯作者：
Mo Dong-Liang
中科院分区：
文献类型：
--
作者：
Shi Wei-Min;Li Xiao-Hua;Liang Cui;Mo Dong-Liang
在无金属条件下，以偕胺肟和二芳基碘鎓盐为原料，通过选择性O-芳基化和顺序[3，3]-重排反应，以高产率合成了多种功能化的2-取代苯并恶唑. O-芳基产物和重排产物都与广泛的敏感官能团相容，如酯，醛，硝基，乙烯基，胺和酰胺基团以及卤化物。以克级分两步制备了具有双苯并恶唑的双齿N-配体。
A variety of functionalized 2‐substituted benzoxazoles can be prepared in good yields from amidoximes and diaryliodonium salts by selectiveO‐arylation and sequential [3,3]‐rearrangement under metal‐free conditions.O‐arylation of amidoximes was promoted by 3 Å molecule sieves in the absence of a base and a sequential TFA‐mediated [3,3]‐rearrangement was used to synthesize 2‐substituted benzoxazoles. Both of theO‐aryl products and rearrangement products were compatible with a broad range of sensitive functional groups such as ester, aldehyde, nitro, vinyl, amine, and amide groups in addition to halides. A bidentateN‐ligand with double benzoxazoles was prepared at gram‐scale in two steps.