化学
区域选择性
炔烃
三氟甲磺酸
催化作用
组合化学
三氟甲基磺酸三甲基硅烷基酯
重氮甲烷
有机合成
钌
有机化学
药物化学
作者
Lu Chen,Ya Li,Xiaoyin Bai,Dian Dong,Ming Pan,Ling Huang,Rui Huang,Xiangyun Long,Yibiao Li
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-09-14
卷期号:25 (38): 7025-7029
被引量:1
标识
DOI:10.1021/acs.orglett.3c02623
摘要
A new approach is proposed for the divergent and regioselective synthesis of (E)-2-bromo-1-phenylvinyl trifluoromethanesulfonates through alkyne difunctionalization by employing a compatible system of abundantly available alkynes, N-bromosuccinimide (NBS), and trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed by ruthenium(III) acetate [Ru(OAc)3]. It is a novel method for the preparation of vinyl triflate and it offers a fundamental basis for the development of advanced functional compounds, including drugs and organic functional materials. Unlike previously reported methods, the proposed protocol can tolerate a broad range of functional groups. Alkynes derived from bioactive molecules, such as l(-)-borneol, demonstrate the potential value of this new reaction in organic synthesis.
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