Issue 9, 2017

Mechanistic insight into the selective olefin-directed oxidative carbocyclization and borylation by a palladium catalyst: a theoretical study

Abstract

A mechanistic study of palladium-catalyzed oxidative carbocyclization and borylation of allenes was carried out by using density functional theory (DFT) calculations. A subtle change in the reaction conditions can cause the reaction to produce either cyclobutene product or alkenylboron compound with high chemoselectivity. Acetic acid solvent gives the alkenylboron compound as the major product, while methanol solvent favors the formation of the cyclobuteneboron product. Our calculations account for the observed solvent-controlled chemoselectivity. Lowering the polarity of the solvent disfavors the olefin insertion step and the formation of cyclobuteneboron product.

Graphical abstract: Mechanistic insight into the selective olefin-directed oxidative carbocyclization and borylation by a palladium catalyst: a theoretical study

Supplementary files

Article information

Article type
Paper
Submitted
05 12 2016
Accepted
29 12 2016
First published
17 1 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 5013-5018

Mechanistic insight into the selective olefin-directed oxidative carbocyclization and borylation by a palladium catalyst: a theoretical study

X. Zheng, L. Nie, Y. Li, S. Liu, F. Zhao, X. Zhang, X. Wang and T. Liu, RSC Adv., 2017, 7, 5013 DOI: 10.1039/C6RA27752G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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