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Published February 1, 2017 | Version Supplemental Material + Accepted Version
Journal Article Open

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

Creators

Abstract

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.

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.

Attached Files

Accepted Version - jacs_2E6b12114.pdf

Supplemental Material - ja6b12114_si_001.pdf

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ja6b12114_si_001.pdf

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Additional details

Identifiers

Eprint ID
73231
DOI
10.1021/jacs.6b12114
Resolver ID
CaltechAUTHORS:20170104-153320118

Funding

NSF
CHE-1205646
NSF
CHE-1212767
Bristol-Myers Squibb
Resnick Sustainability Institute
Dow Chemical
Natural Sciences and Engineering Research Council of Canada (NSERC)
Shanghai Institute of Organic Chemistry (SIOC)

Dates

Created
2017-01-04
Created from EPrint's datestamp field
Updated
2021-11-11
Created from EPrint's last_modified field

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Caltech groups
Resnick Sustainability Institute