Abstract
Reduction reactions of unsaturated compounds are fundamental transformations in synthetic chemistry. In this context, the reduction of polarized double bonds such as carbonyl or C=C motifs can be achieved by hydrogenation reactions. We describe here a highly chemoselective Mn(I)-based PNP pincer catalyst for the hydrosilylation of aldehydes and ketones employing polymethylhydrosiloxane (PMHS) as inexpensive hydrogen donor.Graphic abstract
Highlights
The reduction of polarized double bonds such as carbonyl motifs is among the most important transformations in organic synthesis
We have described an efficient manganese-catalyzed hydrosilylation of aldehydes and ketones with the inexpensive siloxane PMHS, which is a byproduct in industry
In the case of aldehydes, challenging substrates featuring C–C double bonds were chosen which are important in the fragrance industry
Summary
The reduction of polarized double bonds such as carbonyl motifs is among the most important transformations in organic synthesis. We wondered if the same complex is capable of undergoing hydrosilylation reactions of carbonyl compounds and whether the substrate scope could be extended to ketones (Scheme 1). Complexes 1 and 2 gave moderate to good conversion whereas compounds 3 and 4 did not show any reactivity for the hydrosilylation of 4-fluoroacetophenone.
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