NDLI: A theoretical study on the mechanisms of intermolecular hydroacylation of aldehyde catalyzed by neutral and cationic rhodium complexes

Content Provider	Springer Nature Link
Author	Wang, Min Zhang, Xin Chen, Zhuo Tang, YanHui Lei, Ming
Copyright Year	2014
Abstract	In this paper, we used density functional theory (DFT) computations to study the mechanisms of the hydroacylation reaction of an aldehyde with an alkene catalyzed by Wilkinson’s catalyst and an organic catalyst 2-amino-3-picoline in cationic and neutral systems. An aldehyde’s hydroacylation includes three stages: the C-H activation to form rhodium hydride (stage I), the alkene insertion into the Rh-H bond to give the Rh-alkyl complex (stage II), and the C-C bond formation (stage III). Possible pathways for the hydroacylation originated from the trans and cis isomers of the catalytic cycle. In this paper, we discussed the neutral and cationic pathways. The rate-determining step is the C-H activation step in neutral system but the reductive elimination step in the cationic system. Meanwhile, the alkyl group migration-phosphine ligand coordination pathway is more favorable than the phosphine ligand coordination-alkyl group migration pathway in the C-C formation stage. Furthermore, the calculated results imply that an electron-withdrawing group may decrease the energy barrier of the C-H activation in the benzaldehyde hydroacylation.
Starting Page	1264
Ending Page	1275
Page Count	12
File Format	PDF
ISSN	16747291
Journal	Science in China Series B: Chemistry
Volume Number	57
Issue Number	9
e-ISSN	18691870
Language	English
Publisher	Science China Press
Publisher Date	2014-06-07
Publisher Place	Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	C-H activation DFT hydroacylation metal organic cooperative catalyst reaction mechanism rhodium complex Chemistry/Food Science
Content Type	Text
Resource Type	Article
Subject	Chemistry

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