Toutov, Anton A. and Betz, Kerry N. and Haibach, Michael C. and Romine, Andrew M. and Grubbs, Robert H. (2016) Sodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes. Organic Letters, 18 (22). pp. 5776-5779. ISSN 1523-7060. doi:10.1021/acs.orglett.6b01687. https://resolver.caltech.edu/CaltechAUTHORS:20161114-093917870
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Abstract
An O–Si bond construction protocol employing abundantly available and inexpensive NaOH as the catalyst is described. The method enables the cross-dehydrogenative coupling of an alcohol and hydrosilane to directly generate the corresponding silyl ether under mild conditions and without the production of stoichiometric salt byproducts. The scope of both coupling partners is excellent, positioning the method for use in complex molecule and materials science applications. A novel Si-based cross-coupling reagent is also reported.
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| Additional Information: | © 2016 American Chemical Society. Received: June 10, 2016; Revised: October 11, 2016; Publication Date (Web): November 9, 2016. This work was supported by the NSF under the CCI Center for Selective C–H Functionalization (CHE-1205646) and under CHE-1212767. A.A.T. is grateful to the Resnick Sustainability Institute at Caltech and to Dow Chemical for a predoctoral fellowship and to NSERC for a PGS D fellowship. We thank S. Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. M. Shahgoli and N. Torian (Caltech) are acknowledged for assistance with high-resolution mass spectrometry. The authors declare no competing financial interest. | ||||||||||||
| Group: | Resnick Sustainability Institute | ||||||||||||
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| Issue or Number: | 22 | ||||||||||||
| DOI: | 10.1021/acs.orglett.6b01687 | ||||||||||||
| Record Number: | CaltechAUTHORS:20161114-093917870 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20161114-093917870 | ||||||||||||
| Official Citation: | Sodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes Anton A. Toutov, Kerry N. Betz, Michael C. Haibach, Andrew M. Romine, and Robert H. Grubbs Organic Letters 2016 18 (22), 5776-5779 DOI: 10.1021/acs.orglett.6b01687 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 71983 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||
| Deposited On: | 15 Nov 2016 23:54 | ||||||||||||
| Last Modified: | 11 Nov 2021 04:54 |
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