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Issue 5, 2015
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Heterogeneous double-activation catalysis: Rh complex and tertiary amine on the same solid surface for the 1,4-addition reaction of aryl- and alkylboronic acids

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Abstract

Double-activation catalysis by a rhodium complex/tertiary amine catalyst for the 1,4-addition of organoboronic acids was investigated. A rhodium complex and a tertiary amine were co-immobilized on the same silica surface by silane-coupling reactions followed by complexation of the Rh species. Structures of the Rh complex and tertiary amine on the silica surface were determined by solid-state 13C and 29Si MAS NMR, XAFS, and XPS measurements. The immobilized tertiary amine accelerated the Rh-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone. The role of the anchored tertiary amine in the 1,4-addition reaction was clarified by solid-state 11B MAS NMR: it activates the arylboronic acid forming a four-coordinate boron species, which then accelerates the transmetallation step in the Rh complex-catalyzed 1,4-addition. The silica-supported Rh complex/tertiary amine catalyst system could be applicable to the reaction of various aryl- and even alkyl-boronic acids.

Graphical abstract: Heterogeneous double-activation catalysis: Rh complex and tertiary amine on the same solid surface for the 1,4-addition reaction of aryl- and alkylboronic acids

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Article information


Submitted
28 Jan 2015
Accepted
16 Feb 2015
First published
18 Feb 2015

Catal. Sci. Technol., 2015,5, 2714-2727
Article type
Paper
Author version available

Heterogeneous double-activation catalysis: Rh complex and tertiary amine on the same solid surface for the 1,4-addition reaction of aryl- and alkylboronic acids

H. Noda, K. Motokura, W. Chun, A. Miyaji, S. Yamaguchi and T. Baba, Catal. Sci. Technol., 2015, 5, 2714
DOI: 10.1039/C5CY00133A

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