The mechanism of the gold(i)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol via 4-endo-dig cyclization

被引：5
|
作者：
Sorbelli, Diego [1 ]
Segato, Jacopo [2 ]
Del Zotto, Alessandro [2 ]
Belpassi, Leonardo [3 ]
Zuccaccia, Daniele [2 ]
Belanzoni, Paola [1 ,3 ]
机构：
[1] Univ Perugia, Dept Chem Biol & Biotechnol, Via Elce Sotto 8, I-06123 Perugia, Italy
[2] Univ Udine, Sez Chim, Dipartimento Sci Agroalimentari Ambientali & Anim, Via Cotonificio 108, I-33100 Udine, Italy
[3] Univ Perugia, Dept Chem Biol & Biotechnol, Inst Chem Sci & Technol Giulio Natta CNR CNR SCIT, Via Elce Sotto 8, I-06123 Perugia, Italy
来源：
DALTON TRANSACTIONS | 2021年 / 50卷 / 15期
关键词：
GOLD CATALYSIS SYNTHESIS; INDUSTRIAL PERSPECTIVE; COUNTER ANIONS; PIVOTAL ROLE; AU-X; ALKOXYLATION; HYDRATION; ALKYNES; SOLVENT;
D O I：
10.1039/d1dt00080b
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
With the aim of rationalizing the experimental counterion- and solvent-dependent reactivity in the gold(i)-catalyzed Meyer-Schuster rearrangement of 1-phenyl-2-propyn-1-ol, a computational mechanistic study unraveled the unexpected formation of a gold-oxetene intermediate via commonly unfavorable 4-endo-dig cyclization triggered by the counterion in low polarity solvents.
引用
收藏
页码：5154 / 5160
页数：7
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