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Synfacts 2020; 16(05): 0565
DOI: 10.1055/s-0040-1707918
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ring-Opening Hydroboration of Epoxides Catalyzed by a Silica-Supported Organolanthanum Complex

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Wang Z, Patnaik S, Eedugurala N, Manzano JS, Slowing II, Kobayashi T, Sadow AD. * Pruski M. * U.S. Department of Energy and Iowa State University, Ames, USA
Silica-Supported Organolanthanum Catalysts for C−O Bond Cleavage in Epoxides.

J. Am. Chem. Soc. 2020;
142: 2935-2947
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Publication History

Publication Date:
20 April 2020 (online)

 
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Key words

lanthanum catalysis - mesoporous silica - hydroboration - epoxides

Significance

An organolanthanum complex immobilized on mesoporous silica nanoparticles ([La]@MSN700), prepared as shown in equation 1, catalyzed the ring-opening hydroboration of epoxides with pinacolborane to give the corresponding boryl ethers in 87–100% NMR yield (eq. 2).


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Comment

[La]@MSN700 was characterized by means of mass balance of grafting, surface alcoholysis reactions, elemental analysis, and DRIFTS, STEM, EDX, and SSNMR spectroscopies. In the reaction of styrene oxide with pinacolborane, the catalyst was reused five times with a gradual loss of its catalytic activity.


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