Magnesium-catalyzed hydrosilylation of a,b-unsaturated esters

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dc.contributor.author Lampland, Nicole
dc.contributor.author Sadow, Aaron
dc.contributor.author Pindwal, Aradhana
dc.contributor.author Neal, Steven
dc.contributor.author Schlauderaff, Shealyn
dc.contributor.author Ellern, Arkady
dc.contributor.author Sadow, Aaron
dc.contributor.department Chemistry
dc.date 2018-02-17T06:56:00.000
dc.date.accessioned 2020-06-30T01:18:32Z
dc.date.available 2020-06-30T01:18:32Z
dc.date.copyright Thu Jan 01 00:00:00 UTC 2015
dc.date.issued 2015-08-01
dc.description.abstract <p>To<sup>M</sup>MgHB(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> (<strong>1</strong>, To<sup>M</sup> = tris(4,4-dimethyl-2-oxazolinyl)phenylborate) catalyzes the 1,4-hydrosilylation of α,β-unsaturated esters. This magnesium hydridoborate compound is synthesized by the reaction of To<sup>M</sup>MgMe, PhSiH<sub>3</sub>, and B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>. Unlike the transient To<sup>M</sup>MgH formed from the reaction of To<sup>M</sup>MgMe and PhSiH<sub>3</sub>, the borate adduct <strong>1</strong> persists in solution and in the solid state. Crystallographic characterization reveals tripodal coordination of the HB(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> moiety to the six-coordinate magnesium center with a ∠Mg–H–B of 141(3)°. The pathway for formation of <strong>1</strong> is proposed to involve the reaction of To<sup>M</sup>MgMe and a PhSiH<sub>3</sub>/B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> adduct because the other possible intermediates, To<sup>M</sup>MgH and To<sup>M</sup>MgMeB(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>, react to give an intractable black solid and To<sup>M</sup>MgC<sub>6</sub>F<sub>5</sub>, respectively. Under catalytic conditions, silyl ketene acetals are isolated in high yield from the addition of hydrosilanes to α,β-unsaturated esters with <strong>1</strong> as the catalyst.</p>
dc.description.comments <p>This article is from <em>Chemical Science</em> 6 (2015): 6901, doi: <a href="http://dx.doi.org/10.1039/c5sc02435h" target="_blank">10.1039/c5sc02435h</a>. Posted with permission.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/chem_pubs/223/
dc.identifier.articleid 1211
dc.identifier.contextkey 7889338
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/223
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/14664
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/223/2015_SadowAD_MagnesiumCatalyzedHydrosilylation.pdf|||Fri Jan 14 22:42:52 UTC 2022
dc.source.uri 10.1039/c5sc02435h
dc.subject.disciplines Chemistry
dc.subject.keywords catalysis
dc.subject.keywords esters
dc.subject.keywords Hydrosilylation
dc.subject.keywords Crystallographic characterization
dc.subject.keywords Hydrosilanes
dc.subject.keywords Silyl ketene acetal
dc.title Magnesium-catalyzed hydrosilylation of a,b-unsaturated esters
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication a9d328ff-ec5e-4d1d-8c2f-aed9d5a290ed
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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