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- Title
CO<sub>2</sub> Hydroboration: Impact of the Boryl Moieties on the Reactivity of Four Bis(boryl)acetal Compounds toward 2,6‐Diisopropylaniline.
- Authors
Desmons, Sarah; Zhou, Yu; Zhang, Dan; Jarava‐Barrera, Carlos; Coffinet, Anaïs; Simonneau, Antoine; Vendier, Laure; Luo, Gen; Bontemps, Sébastien
- Abstract
The hydroboration of CO2 into bis(boryl)acetal (BBA) compounds is an important transformation, since it enabled to selectively reduce CO2 by 4e‐and to subsequently use the BBA compounds as C1 and Cn sources. However, the influence of the nature of the boryl moieties on the reactivity of BBA compounds has not been evaluated so far. In the present study, four BBA compounds – including two new ones – were reacted with 2,6‐diisopropylaniline to afford the expected imine. Significant differences in the rate of the reaction from minutes to weeks have been observed depending on the BBA used, showing the importance of the nature of the boryl moieties. Theoretical investigations enabled to propose a mechanism involving the addition of the aniline to the BBA as the rate‐determining step and to determine that the steric hindrance of the BBA compounds is the main factor driving the rate of this condensation reaction.
- Subjects
HYDROBORATION; MOIETIES (Chemistry); STERIC hindrance; CONDENSATION reactions; CARBON dioxide
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 30, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300525