Ruthenium-Catalyzed Formal Dehydrative [4 + 2] Cycloaddition of Enamides and Alkynes for the Synthesis of Highly Substituted Pyridines: Reaction Development and Mechanistic Study

Journal of the American Chemical Society

Volumn 137, Issue 29, 2015, Pages 9489-9496

  Wu, Jicheng ^a   Xu, Wenbo ^b   Yu, Zhi Xiang ^b   Wang, Jian ^a  

^a Tsinghua University   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL REACTIONS; DENSITY FUNCTIONAL THEORY; HYDROCARBONS; PYRIDINE; REACTION INTERMEDIATES;

ALKYNE INSERTIONS; CARBONYL GROUPS; CHEMICAL EQUATIONS; DFT CALCULATION; HIGH-EFFICIENCY; MECHANISTIC STUDIES; REGIOCHEMISTRY; [4 + 2] CYCLOADDITION;

RUTHENIUM;

ACETIC ACID; ALKYNE DERIVATIVE; AMIDE; CARBONYL DERIVATIVE; ENAMIDE DERIVATIVE; PYRIDINE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG; ALKYNE; PYRIDINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; MECHANICS; PROTON TRANSPORT; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; QUANTUM THEORY;

ALKYNES; AMIDES; CATALYSIS; CYCLOADDITION REACTION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRIDINES; QUANTUM THEORY; RUTHENIUM;

EID: 84938301138     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b06400     Document Type: Article

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101. The computed activation free energies here in solution are higher than the expected value of the experiment, considering that the reaction was carried out at 100 °C. One of the sources for the overestimation of the reaction activation free energy is the entropy overestimation in solution: we used the gas-phase computed entropies as the estimated entropies in solution, and this approximation introduces entropy overestimation for the present two-molecule to one-molecule process, which converts two molecules (IN13 and HOAc) to one molecule (IN6).