Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules

Shi-Chao Ren, Feng-Lian Zhang, Ai-Qing Xu, Yinuo Yang, Min Zheng, Xiaoguo Zhou (), Yao Fu () and Yi-Feng Wang ()
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Shi-Chao Ren: University of Science and Technology of China
Feng-Lian Zhang: University of Science and Technology of China
Ai-Qing Xu: University of Science and Technology of China
Yinuo Yang: University of Science and Technology of China
Min Zheng: University of Science and Technology of China
Xiaoguo Zhou: University of Science and Technology of China
Yao Fu: University of Science and Technology of China
Yi-Feng Wang: University of Science and Technology of China

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Organoboron compounds are highly valuable in synthetic chemistry. In particular, α-borylcarbonyl compounds have shown versatile synthetic applications, owing to fruitful chemistries of both the boryl and carbonyl moieties. However, the synthesis of these molecules still remains tedious and time-consuming. Here we report a straightforward and practical route to synthesize α-borylcarbonyl molecules based on a regioselective radical α-borylation of α,β-unsaturated carbonyl compounds. The reaction features unusual α-regioselectivity and high functional-group compatibility. Further synthetic applications of new α-borylated products were also demonstrated. DFT and kinetic studies implicated that the α-regioselectivity of β-aryl-α,β-unsaturated carbonyl compounds was determined by the thermodynamically more favorable radical α-addition step, whereas the formation of α-addition products from β-alkyl-α,β-unsaturated carbonyl compounds was driven by an energetically favored hydrogen atom transfer step. Given that α,β-unsaturated carbonyl compounds can be easily obtained in abundance and variety, this method enjoys great advantages in diverse and economical synthesis of valuable α-borylcarbonyl molecules.

Date: 2019
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DOI: 10.1038/s41467-019-09825-3

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