Unprecedented multifunctionality of Grubbs and Hoveyda–Grubbs catalysts: competitive isomerization, hydrogenation, silylation and metathesis occurring in solution and on solid phase
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Date
2017-04-09
Journal Title
Journal ISSN
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Publisher
MDPI
Abstract
Description
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.
Keywords
Cross-metathesis, Reduction, Silylation, Isomerization, Solid-phase, Alkenes, Ruthenium Catalyst