Elucidation of the Mechanism of Silver-Catalyzed Inverse Electron-Demand Diels-Alder (IEDDA) Reaction of 1,2-Diazines and Siloxy Alkynes

被引：3
|
作者：
Naz Avci, Oykum [1 ]
Catak, Saron [1 ]
Dereli, Busra [2 ]
Aviyente, Viktorya [1 ]
Dedeoglu, Burcu [3 ]
机构：
[1] Bogazici Univ Bebek, Dept Chem, TR-34342 Istanbul, Turkey
[2] King Abdullah Univ Sci & Technol, KCC, Thuwal 239556900, Saudi Arabia
[3] Gebze Tech Univ Gebze, Dept Chem, TR-41400 Kocaeli, Turkey
来源：
CHEMCATCHEM | 2020年 / 12卷 / 01期
关键词：
DFT calculations; transition metal catalysis; silver; inverse electron demand Diels Alder reaction; cycloaddition; HETEROCYCLIC AZADIENES; DENSITY FUNCTIONALS; NONCOVALENT INTERACTIONS; THERMOCHEMICAL KINETICS; LEWIS-ACID; SOLUTES; MODELS;
D O I：
10.1002/cctc.201901525
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Density functional theory (DFT) calculations were utilized to reveal the effect of highly efficient transition metal catalysis in inverse electron demand Diels-Alder (IEDDA) reactions. The silver-catalyzed IEDDA reactions of 1,2-diazines and siloxy alkynes were investigated to highlight the effect of the catalyst and its mode of action. Two different reaction pathways, concerted and stepwise, were explored as well as the uncatalyzed reaction. Computations elucidate the details of the highly efficient Ag catalyst in IEDDA reaction, and are consistent with previous experimental studies. The mode of action for the catalyst is fully revealed and its specific effect on the regioselectivity/specificity of the reaction is established.
引用
收藏
页码：366 / 372
页数：7
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