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Room-Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity.
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-04-24 , DOI: 10.1002/anie.202004758 Teng Wei Ng 1 , Gang Liao 1 , Kai Kiat Lau 1 , Hui-Jie Pan 1 , Yu Zhao 1, 2
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-04-24 , DOI: 10.1002/anie.202004758 Teng Wei Ng 1 , Gang Liao 1 , Kai Kiat Lau 1 , Hui-Jie Pan 1 , Yu Zhao 1, 2
Affiliation
We report herein an unprecedented highly efficient Guerbet‐type reaction at room temperature (catalytic TON up to >6000). This β‐alkylation of secondary methyl carbinols with primary alcohols has significant advantage of delivering higher‐order secondary alcohols in an economical, redox‐neutral fashion. In addition, the first enantioselective Guerbet reaction has also been achieved using a commercially available chiral ruthenium complex to deliver secondary alcohols with moderate yield and up to 92 % ee . In both reactions, the use of a traceless ketone promoter proved to be beneficial for the catalytic efficiency.
中文翻译:
具有前所未有的催化效率和对映选择性的室温Guerbet反应。
我们在此报告了室温下前所未有的高效Guerbet型反应(催化TON高达> 6000)。仲甲基甲醇与伯醇的这种β-烷基化具有显着的优势,即可以经济,氧化还原中性的方式提供高阶仲醇。此外,还使用市售的手性钌配合物实现了第一个对映选择性Guerbet反应,以中等收率和高达92%ee的速率输送仲醇。在两个反应中,使用无痕酮助催化剂均被证明对催化效率有利。
更新日期:2020-07-01
中文翻译:
具有前所未有的催化效率和对映选择性的室温Guerbet反应。
我们在此报告了室温下前所未有的高效Guerbet型反应(催化TON高达> 6000)。仲甲基甲醇与伯醇的这种β-烷基化具有显着的优势,即可以经济,氧化还原中性的方式提供高阶仲醇。此外,还使用市售的手性钌配合物实现了第一个对映选择性Guerbet反应,以中等收率和高达92%ee的速率输送仲醇。在两个反应中,使用无痕酮助催化剂均被证明对催化效率有利。