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Catalysts 2016, 6(9), 141; doi:10.3390/catal6090141

Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature

1
Department of Chemistry, The University of Texas at Austin, Austin, TX 78712, USA
2
Center for Multidimensional Carbon Materials (CMCM), Institute for Basic Science (IBS), Ulsan National Institute of Science and Technology (UNIST), Ulsan 44919, Korea
3
Department of Chemistry and Department of Energy Engineering, Ulsan National Institute of Science and Technology (UNIST), Ulsan 44919, Korea
*
Author to whom correspondence should be addressed.
Academic Editor: Federico Cisnetti
Received: 13 August 2016 / Revised: 1 September 2016 / Accepted: 2 September 2016 / Published: 12 September 2016
(This article belongs to the Special Issue Tailor-Made NHC Ligands)
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Abstract

An isolable N,N’-diamidocarbene (DAC) was previously shown to promote the B–H bond activation of various BH3 complexes. The resultant DAC–BH3 adducts facilitated olefin hydroborations under mild conditions and in the absence of exogenous initiators. The substrate scope for such transformations was further explored and is described herein. While organoboranes were obtained in quantitative yields from various terminal and internal olefins, use of the latter substrates resulted in intramolecular ring-expansion of the newly formed DAC–borane adducts. View Full-Text
Keywords: hydroboration; carbenes; organocatalysis; Lewis adducts; diamidocarbene hydroboration; carbenes; organocatalysis; Lewis adducts; diamidocarbene
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Lastovickova, D.N.; Bielawski, C.W. Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature. Catalysts 2016, 6, 141.

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