NDLI: Theoretical insights into the [4 + 2]/retro [4 + 2] cycloaddition approach to the synthesis of biaryls and polycyclic aromatics

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Theoretical insights into the [4 + 2]/retro [4 + 2] cycloaddition approach to the synthesis of biaryls and polycyclic aromatics

Content Provider	Springer Nature Link
Author	Li, XinYao Xu, JiaXi
Copyright Year	2013
Abstract	A domino [4 + 2]/retro [4 + 2] cycloaddition process of cyclohexadienes with arylethynes or benzyne providing access to biaryls and polycyclic aromatics has been studied theoretically using density functional theory calculations. It has been found that the initial Diels-Alder (D-A) reaction acts as the rate-determining step and the consequent [4 + 2] cycloreversion reaction is feasible under the conditions used. Furthermore, the D-A reaction affects the regioselectivity, the origin of which is essentially derived from the good match of orbital coefficients between dienes and dienophiles as shown by using frontier molecular orbital (FMO) theory. Further investigation of the reactivity reveals that the reactions are predicted to fail to occur if an electron-donor group in the diene or an electron-acceptor group in the dienophile is lacking, as a consequence of the increased FMO energy gap. By further exploring the scope of substrates computationally, benzyne as an active dienophile was predicted to react with a variety of dienes in a cascade reaction under mild conditions with a low energy barrier, with the rate-determining step being the retro [4 + 2] cycloaddition.
Starting Page	633
Ending Page	640
Page Count	8
File Format	PDF
ISSN	16747291
Journal	Science in China Series B: Chemistry
Volume Number	56
Issue Number	5
e-ISSN	18691870
Language	English
Publisher	SP Science China Press
Publisher Date	2013-01-07
Publisher Place	Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	[4 + 2]/retro [4 + 2] cycloaddition biaryls polycyclic aromatics regioselectivity DFT study Chemistry/Food Science
Content Type	Text
Resource Type	Article
Subject	Chemistry

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