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While the one-electron reduction of (CAACMe )BH₂ Br (CAACMe =1-(2,6-diisopropylphenyl)-3,3,5,5-tetramethylpyrrolidin-2-ylidene) yields a hydride-shift isomer of the corresponding tetrahydrodiborane, a further reversible reduction leads to the first stable parent boryl anion, [(CAACMe )BH₂ ]⁻ , which acts as a powerful boron nucleophile.
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Arrowsmith et al. (2018) studied this question.
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