Liu Congrong, Xu Jin, Ding Lianghui, Zhang Haiyun, Xue Yunbo, Yang Fulai
School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu 211167, China.
Org Biomol Chem. 2019 May 8;17(18):4435-4439. doi: 10.1039/c9ob00151d.
An efficient protocol for the synthesis of γ,δ-unsaturated α-chloroketones has been developed via Au-catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement. In the presence of 1 mol% JohnPhosAuCl and 1 mol% NaBArF, a broad range of allylic alcohols smoothly underwent the tandem intermolecular hydroalkoxylation/Claisen rearrangement with aromatic, vinylic or aliphatic chloroalkynes to give structurally diverse γ,δ-unsaturated α-chloroketones in excellent yields. Importantly, high Z/E selectivity was achieved. Other advantages are widespread availability of the substrates, compatibility with a broad range of functional groups and mild reaction conditions.
通过金催化的分子间串联氢烷氧基化/克莱森重排反应，开发了一种高效合成γ,δ-不饱和α-氯代酮的方法。在1 mol%的JohnPhosAuCl和1 mol%的NaBArF存在下，多种烯丙醇能顺利地与芳基、乙烯基或脂肪族氯代炔烃发生分子间串联氢烷氧基化/克莱森重排反应，以优异的产率得到结构多样的γ,δ-不饱和α-氯代酮。重要的是，实现了高Z/E选择性。该方法的其他优点包括底物易于获得、与多种官能团兼容以及反应条件温和。
