Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
J Org Chem. 2017 Apr 21;82(8):4242-4253. doi: 10.1021/acs.joc.7b00238. Epub 2017 Apr 3.
Stable 2-(trimethylsilyl)phenyl trimethylsilyl ethers, readily obtained from the corresponding halogenated phenols in two steps, were identified as novel benzyne precursors. These species were converted to benzynes by a domino reaction of O-desilylation, O-nonaflylation, and β-elimination under mild conditions using nonafluorobutanesulfonyl fluoride (NfF) and tetrabutylammonium triphenyldifluorosilicate (TBAT). The generated benzynes were trapped by various arynophiles to afford a wide variety of benzo-fused heterocycles.
稳定的 2-(三甲基甲硅烷基)苯基三甲基硅基醚，可通过两步反应从相应的卤代苯酚中轻松获得，被鉴定为新型苯炔前体。这些物质在温和条件下使用全氟丁基磺酰氟（NfF）和四丁基三苯基二氟硅烷（TBAT），通过 O-脱甲硅烷基化、O-全氟壬基化和β-消除的多米诺反应转化为苯炔。生成的苯炔被各种芳基亲电试剂捕获，得到了广泛的苯并稠合杂环。
