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Alkali metal hydroxide–catalyzed C(sp)–H bond silylation

Toutov, Anton A. and Betz, Kerry N. and Schuman, David P. and Liu, Wen-Bo and Fedorov, Alexey and Stoltz, Brian M. and Grubbs, Robert H. (2017) Alkali metal hydroxide–catalyzed C(sp)–H bond silylation. Journal of the American Chemical Society, 139 (4). pp. 1668-1674. ISSN 0002-7863. doi:10.1021/jacs.6b12114.

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Disclosed is a mild, scalable, and chemoselective catalytic cross-dehydrogenative C–H bond functionalization protocol for the construction of C(sp)–Si bonds in a single step. The scope of the alkyne and hydrosilane partners is substantial, providing an entry point into various organosilane building blocks and additionally enabling the discovery of a number of novel synthetic strategies. Remarkably, the optimal catalysts are NaOH and KOH.

Item Type:Article
Related URLs:
URLURL TypeDescription Information
Toutov, Anton A.0000-0002-6561-0462
Betz, Kerry N.0000-0001-9118-5909
Liu, Wen-Bo0000-0003-2687-557X
Fedorov, Alexey0000-0001-9814-6726
Stoltz, Brian M.0000-0001-9837-1528
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2016 American Chemical Society. Received: November 23, 2016; Published: December 27, 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 Bristol–Myers Squibb, the Resnick Sustainability Institute at Caltech, and to Dow Chemical for predoctoral fellowships as well as to NSERC for a PGS D fellowship. D.P.S thanks the CCI Center for Selective C–H Functionalization for support. W.-B.L thanks The Shanghai Institute of Organic Chemistry (SIOC) and S.-L. You for a postdoctoral 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. A.A.T. and K.N.B. contributed equally. The authors declare no competing financial interests.
Group:Resnick Sustainability Institute
Funding AgencyGrant Number
Bristol-Myers SquibbUNSPECIFIED
Resnick Sustainability InstituteUNSPECIFIED
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Shanghai Institute of Organic Chemistry (SIOC)UNSPECIFIED
Issue or Number:4
Record Number:CaltechAUTHORS:20170104-153320118
Persistent URL:
Official Citation:Alkali Metal-Hydroxide-Catalyzed C(sp)–H Bond silylation Anton A. Toutov, Kerry N. Betz, David P. Schuman, Wen-Bo Liu, Alexey Fedorov, Brian M. Stoltz, and Robert H. Grubbs Journal of the American Chemical Society 2017 139 (4), 1668-1674 DOI: 10.1021/jacs.6b12114
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:73231
Deposited By: Tony Diaz
Deposited On:04 Jan 2017 23:42
Last Modified:11 Nov 2021 05:13

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