Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature

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 f...

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Main Authors:	Dominika N. Lastovickova, Christopher W. Bielawski
Format:	Article
Language:	English
Published:	MDPI AG 2016-09-01
Series:	Catalysts
Subjects:	hydroboration carbenes organocatalysis Lewis adducts diamidocarbene
Online Access:	http://www.mdpi.com/2073-4344/6/9/141

id	doaj-3b78c3a6aa7f45a5854497a49e34781f
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spelling	doaj-3b78c3a6aa7f45a5854497a49e34781f2020-11-24T23:19:49ZengMDPI AGCatalysts2073-43442016-09-016914110.3390/catal6090141catal6090141Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room TemperatureDominika N. Lastovickova0Christopher W. Bielawski1Department of Chemistry, The University of Texas at Austin, Austin, TX 78712, USACenter for Multidimensional Carbon Materials (CMCM), Institute for Basic Science (IBS), Ulsan National Institute of Science and Technology (UNIST), Ulsan 44919, KoreaAn 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.http://www.mdpi.com/2073-4344/6/9/141hydroborationcarbenesorganocatalysisLewis adductsdiamidocarbene
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Dominika N. Lastovickova Christopher W. Bielawski
spellingShingle	Dominika N. Lastovickova Christopher W. Bielawski Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature Catalysts hydroboration carbenes organocatalysis Lewis adducts diamidocarbene
author_facet	Dominika N. Lastovickova Christopher W. Bielawski
author_sort	Dominika N. Lastovickova
title	Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature
title_short	Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature
title_full	Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature
title_fullStr	Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature
title_full_unstemmed	Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature
title_sort	olefin hydroborations with diamidocarbene–bh3 adducts at room temperature
publisher	MDPI AG
series	Catalysts
issn	2073-4344
publishDate	2016-09-01
description	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.
topic	hydroboration carbenes organocatalysis Lewis adducts diamidocarbene
url	http://www.mdpi.com/2073-4344/6/9/141
work_keys_str_mv	AT dominikanlastovickova olefinhydroborationswithdiamidocarbenebh3adductsatroomtemperature AT christopherwbielawski olefinhydroborationswithdiamidocarbenebh3adductsatroomtemperature
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Olefin Hydroborations with Diamidocarbene–BH3 Adducts at Room Temperature

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