DFT study on α-regioselectivity of photo-organocatalytic functionalization of aldehydes

DFT study on α-regioselectivity of photo-organocatalytic functionalization of aldehydes Journal of Photochemistry and Photobiology A: Chemistry 355 (2018) 9–15 Contents lists available at ScienceDirect Journal of Photochemistry and Photobiology A: Chemistry journal homepa ge: www.elsev ier.com/locate/jphotochem DFT study on a-regioselectivity of photo-organocatalytic functionalization of aldehydes a b, b Yuhua Liu , Haizhu Yu *, Qing-Xiang Guo School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou, Guangdong 510006, China School of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601, China A R T I C L E I N F O A B S T R A C T Article history: Density functional theory (DFT) study has been conducted to elucidate the key mechanistic Received 21 September 2017 Received in revised form 26 October 2017 transformations and the unique a-regioselectivity of alkylidene malonates towards the photoinitiated Accepted 31 October 2017 a-alkylation of aldehydes. The reaction between n-butyl aldehyde and diethyl methylenemalonate was Available online 18 December 2017 chosen as model reaction and the possible reaction pathways were computed. Our calculations reveal that a-alkylation of aldehydes with alkylidene malonates proceeds through a radical–radical coupling Keywords: pathway, instead of the radical chain or radical propagation pathway. This work demonstrates the details Alkylation of the mechanistic framework and rationalizes the a-regioselectivity http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Photochemistry and Photobiology A: Chemistry Elsevier

DFT study on α-regioselectivity of photo-organocatalytic functionalization of aldehydes

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Publisher
Elsevier
Copyright
Copyright © 2017 Elsevier Ltd
ISSN
1010-6030
eISSN
1873-2666
D.O.I.
10.1016/j.jphotochem.2017.10.060
Publisher site
See Article on Publisher Site

Abstract

Journal of Photochemistry and Photobiology A: Chemistry 355 (2018) 9–15 Contents lists available at ScienceDirect Journal of Photochemistry and Photobiology A: Chemistry journal homepa ge: www.elsev ier.com/locate/jphotochem DFT study on a-regioselectivity of photo-organocatalytic functionalization of aldehydes a b, b Yuhua Liu , Haizhu Yu *, Qing-Xiang Guo School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou, Guangdong 510006, China School of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui 230601, China A R T I C L E I N F O A B S T R A C T Article history: Density functional theory (DFT) study has been conducted to elucidate the key mechanistic Received 21 September 2017 Received in revised form 26 October 2017 transformations and the unique a-regioselectivity of alkylidene malonates towards the photoinitiated Accepted 31 October 2017 a-alkylation of aldehydes. The reaction between n-butyl aldehyde and diethyl methylenemalonate was Available online 18 December 2017 chosen as model reaction and the possible reaction pathways were computed. Our calculations reveal that a-alkylation of aldehydes with alkylidene malonates proceeds through a radical–radical coupling Keywords: pathway, instead of the radical chain or radical propagation pathway. This work demonstrates the details Alkylation of the mechanistic framework and rationalizes the a-regioselectivity

Journal

Journal of Photochemistry and Photobiology A: ChemistryElsevier

Published: Mar 15, 2018

References

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