Versatile cobalt-catalyzed regioselective chain-walking double hydroboration of 1,n-dienes to access gem-bis(boryl)alkanes

Ming Hu and Shaozhong Ge ()
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Ming Hu: National University of Singapore
Shaozhong Ge: National University of Singapore

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-14543-2

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