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Palladium-catalyzed coupling reaction of 2-iodobiphenyls with alkenyl bromides for the construction of 9-(diorganomethylidene)fluorenes
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2021-09-07 , DOI: 10.1039/d1ob01547h
Ya-Heng Zhao 1 , Jian-Long Wang 1 , Yun-Bing Zhou 1 , Miao-Chang Liu 1 , Hua-Yue Wu 1
Affiliation  

An atom economical protocol for the construction of 9-(diorganomethylidene)fluorenes through palladium-catalyzed coupling reactions of 2-iodobiphenyls with alkenyl bromides has been reported. The reaction proceeds through the C–H activation/oxidative addition/reduction elimination/intramolecular Heck coupling reaction to afford a series of 9-(diorganomethylidene)fluorenes with good yields. Control experiments demonstrate that a five-membered palladacycle acts as a key intermediate and β-H elimination serves as the rate-limiting step.

中文翻译:

钯催化 2-碘联苯与烯基溴的偶联反应构建 9-(二有机亚甲基)芴

已经报道了通过钯催化的 2-碘联苯与烯基溴的偶联反应构建 9-(二有机亚甲基)芴的原子经济协议。该反应通过C-H活化/氧化加成/还原消除/分子内Heck偶联反应进行,以良好的收率得到一系列9-(二有机亚甲基)芴。对照实验表明,五元钯环作为关键中间体,β-H 消除作为限速步骤。
更新日期:2021-09-14
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