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Catalysts 2017, 7(4), 111; doi:10.3390/catal7040111

Unprecedented Multifunctionality of Grubbs and Hoveyda–Grubbs Catalysts: Competitive Isomerization, Hydrogenation, Silylation and Metathesis Occurring in Solution and on Solid Phase

1
Instituto de Química Rosario (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Argentina
2
Institute of Organic Chemistry, Romanian Academy, 202B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania
*
Authors to whom correspondence should be addressed.
Academic Editor: Keith Hohn
Received: 28 February 2017 / Revised: 30 March 2017 / Accepted: 6 April 2017 / Published: 9 April 2017
(This article belongs to the Special Issue Ruthenium Catalysts)
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Abstract

This contribution showcases the interplay of several non-metathetic reactions (isomerization, silylation and “hydrogen-free” reduction) with metathesis in systems comprising a functionalized olefin and a soluble or resin-immobilized silane. These competing, one-pot reactions occur under activation by second-generation Ru-alkylidene catalysts. Different olefinic substrates were used to study the influence of the substitution pattern on the reaction outcome. Emphasis is placed upon the rarely reported yet important transformations implying a solid phase-supported silane reagent. Catalytic species involved in and reaction pathways accounting for these concurrent processes are evidenced. An unexpected result of this research was the clearly proved partial binding of the olefin to the resin, thereby removing it from the reacting ensemble. View Full-Text
Keywords: cross-metathesis; reduction; silylation; isomerization; solid-phase; olefins; ruthenium catalyst cross-metathesis; reduction; silylation; isomerization; solid-phase; olefins; ruthenium catalyst
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Martinez-Amezaga, M.; Delpiccolo, C.M.L.; Méndez, L.; Dragutan, I.; Dragutan, V.; Mata, E.G. Unprecedented Multifunctionality of Grubbs and Hoveyda–Grubbs Catalysts: Competitive Isomerization, Hydrogenation, Silylation and Metathesis Occurring in Solution and on Solid Phase. Catalysts 2017, 7, 111.

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