Published February 1, 2017
| Supplemental Material + Accepted Version
Journal Article
Open
Alkali metal hydroxide–catalyzed C(sp)–H bond silylation
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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jacs_2E6b12114.pdf
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Additional details
- Eprint ID
- 73231
- DOI
- 10.1021/jacs.6b12114
- Resolver ID
- CaltechAUTHORS:20170104-153320118
- CHE-1205646
- NSF
- CHE-1212767
- NSF
- Bristol-Myers Squibb
- Resnick Sustainability Institute
- Dow Chemical
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Shanghai Institute of Organic Chemistry (SIOC)
- Created
-
2017-01-04Created from EPrint's datestamp field
- Updated
-
2021-11-11Created from EPrint's last_modified field
- Caltech groups
- Resnick Sustainability Institute