化学
区域选择性
合成子
废止
分子内力
炔烃
芳构化
炔丙基
呋喃
部分
药物化学
亲核细胞
催化作用
立体化学
三键
亲核加成
有机化学
双键
作者
Min Wu,Yi Wang,Jing Zhou,Ting Wang,Hui Gao,Zhi Zhou,Wei Yi
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-04-03
卷期号:25 (14): 2394-2399
被引量:2
标识
DOI:10.1021/acs.orglett.3c00377
摘要
A variety of 2,3,5-trisubstituted furans were synthesized by virtue of a Rh(III)-catalyzed vinylic C-H coupling of N-enoxyimides with propargyl alcohols or amines. In this protocol, N-enoxyimides served as a one-oxygen and two-carbon synthon and the -OH/-NHR moiety in the alkynes was found to be crucial for realizing the desired chemo-/regioselectivity. Detailed experimental mechanistic studies together with DFT calculations clarified the sequential C-H activation/regioselective alkyne insertion/simultaneous O-N bond cleavage and hydrogen transfer/intramolecular nucleophilic addition/aromatization reaction path, which involved a distinctive Rh(V) carbene species as the active intermediate.
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