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Issue 2, 2019
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Anti-Markovnikov terminal and gem-olefin hydrosilylation using a κ4-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage

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Abstract

The phosphine-substituted α-diimine Ni precursor, (Ph2PPrDI)Ni, has been found to catalyze alkene hydrosilylation in the presence of Ph2SiH2 with turnover frequencies of up to 124 h−1 at 25 °C (990 h−1 at 60 °C). Moreover, the selective hydrosilylation of allylic and vinylic ethers has been demonstrated, even though (Ph2PPrDI)Ni is known to catalyze allyl ester C–O bond hydrosilylation. At 70 °C, this catalyst has been found to mediate the hydrosilylation of ten different gem-olefins, with turnover numbers of up to 740 under neat conditions. Prior and current mechanistic observations suggest that alkene hydrosilylation takes place though a Chalk–Harrod mechanism following phosphine donor dissociation.

Graphical abstract: Anti-Markovnikov terminal and gem-olefin hydrosilylation using a κ4-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage

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Supplementary files

Article information


Submitted
21 Nov 2018
Accepted
22 Nov 2018
First published
23 Nov 2018

Dalton Trans., 2019,48, 461-467
Article type
Paper
Author version available

Anti-Markovnikov terminal and gem-olefin hydrosilylation using a κ4-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage

C. L. Rock and R. J. Trovitch, Dalton Trans., 2019, 48, 461
DOI: 10.1039/C8DT04608E

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