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Base‐Free Selective O‐Arylation and Sequential [3,3]‐Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2‐Substituted Benzoxazoles
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-09-29 , DOI: 10.1002/adsc.201700906
Wei-Min Shi 1 , Xiao-Hua Li 1 , Cui Liang 1 , Dong-Liang Mo 1
Affiliation  

A variety of functionalized 2‐substituted benzoxazoles can be prepared in good yields from amidoximes and diaryliodonium salts by selective O‐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 the O‐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 bidentate N‐ligand with double benzoxazoles was prepared at gram‐scale in two steps.

中文翻译:

无碱选择性O-芳基化和酰胺基肟与二芳基碘鎓盐的顺序[3,3]-重排:2-取代的苯并恶唑的合成

在无金属条件下,可以通过选择性O芳基化和顺序[3,3]重排,从ox胺肟和二芳基碘鎓盐中以高收率制备各种功能化的2-取代苯并恶唑。ø偕胺肟的-arylation用3埃分子筛在不存在碱的和促进连续TFA介导的,使用[3,3] -rearrangement以合成2-取代的苯并恶唑。两者的ø -芳基产品和重排产物用宽范围敏感的官能团,如酯,醛,硝基,乙烯基,胺和酰胺基团除了卤化物的兼容。分两步以克规模制备了带有双苯并恶唑的双齿N-配体。
更新日期:2017-09-29
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