NDLI: 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

Content Provider	Royal Society of Chemistry (RSC)
Author	Miyaji, Akimitsu Noda, Hiroto Chun, Wang-Jae Yamaguchi, Sho Baba, Toshihide Motokura, Ken
Copyright Year	2015
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.
Starting Page	2714
Ending Page	2727
Page Count	14
File Format	HTM / HTML PDF
ISSN	20444753
Volume Number	5
Issue Number	5
Journal	Catalysis Science & Technology
DOI	10.1039/c5cy00133a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Cyclohexenone Acid Boron Amine Rhodium Magic angle spinning Addition reaction Nuclear magnetic resonance Aryl Transmetalation Silicon dioxide
Content Type	Text
Resource Type	Article
Subject	Catalysis

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