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https://doi.org/10.1038/s41467-020-14543-2
Title: | Versatile cobalt-catalyzed regioselective chain-walking double hydroboration of 1,n-dienes to access gem-bis(boryl)alkanes | Authors: | Hu, M. Ge, S. |
Issue Date: | 2020 | Publisher: | Nature Research | Citation: | Hu, M., Ge, S. (2020). Versatile cobalt-catalyzed regioselective chain-walking double hydroboration of 1,n-dienes to access gem-bis(boryl)alkanes. Nature Communications 11 (1) : 765. ScholarBank@NUS Repository. https://doi.org/10.1038/s41467-020-14543-2 | Rights: | Attribution 4.0 International | Abstract: | Double hydroboration of dienes is the addition of a hydrogen and a boryl group to the two double bonds of a diene molecule and represents a straightforward and effective protocol to prepare synthetically versatile bis(boryl)alkanes, provided that this reaction occurs selectively. However, this reaction can potentially yield several isomeric organoboron products, and it still remains a challenge to control the regioselectivity of this reaction, which allows the selective production of a single organoboron product, in particular, for a broad scope of dienes. By employing a readily available cobalt catalyst, here we show that this double hydroboration yields synthetically useful gem-bis(boryl)alkanes with excellent regioselectivity. In addition, the scope of dienes for this reaction is broad and encompasses a wide range of conjugated and non-conjugated dienes. Furthermore, mechanistic studies indicate that this cobalt-catalyzed double hydroboration occurs through boryl-directed chain-walking hydroboration of alkenylboronates generated from anti-Markovnikov 1,2-hydroboration of 1,n-diene. © 2020, The Author(s). | Source Title: | Nature Communications | URI: | https://scholarbank.nus.edu.sg/handle/10635/198124 | ISSN: | 2041-1723 | DOI: | 10.1038/s41467-020-14543-2 | Rights: | Attribution 4.0 International |
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