Progress in the Syntheses of α-Boryl Carbonyl Compounds

doi:10.6023/cjoc202303025

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1706-1712.DOI: 10.6023/cjoc202303025 Previous Articles Next Articles

Special Issue: 有机硼化学专辑

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α-硼取代羰基类化合物的合成进展

陈志豪^a, 范奇^b, 尹标林^b, 李清江^a, 王洪根^a^,^*()

a 中山大学药学院广东省手性分子与药物发现重点实验室广州 510006
b 华南理工大学化学与化工学院广东省功能分子工程重点实验室广州 510640

收稿日期:2023-03-17 修回日期:2023-04-14 发布日期:2023-04-26
通讯作者: 王洪根
基金资助:
国家自然科学基金(22022114); 国家自然科学基金(21971261); 广东省基础与应用基础研究基金联合基金(2020A1515010624); 广东珠江人才计划本土创新科研团队项目基金(2017BT01Y093)

Progress in the Syntheses of α-Boryl Carbonyl Compounds

Zhihao Chen^a, Qi Fan^b, Biaolin Yin^b, Qingjiang Li^a, Honggen Wang^a()

a Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006
b Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640

Received:2023-03-17 Revised:2023-04-14 Published:2023-04-26
Contact: Honggen Wang
Supported by:
National Natural Science Foundation of China(22022114); National Natural Science Foundation of China(21971261); Guangdong Basic and Applied Basic Research Foun- dation(2020A1515010624); Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(2017BT01Y093)

α-Boryl carbonyl compounds have traditionally been considered thermodynamically unstable and prone to undergo 1,3-boron migration. In recent years, with the development and understanding of sp³-hybridized boron or tetra-coordinated boron, methods for synthesizing stable and separable α-boryl carbonyl compounds have been actively developed. These methods include the insertion reaction of borane with diazo esters, sulfur ylides and other carbene precursors, the free-radical borylation reaction of α,β-unsaturated carbonyl compounds, and late-stage structural modification reactions of boron-contain- ing compounds. The recent advances in the synthesis of α-boryl carbonyl compounds are reviewed based on different reaction types, and the existing challenges and future research directions are discussed.

Key words: carbene precursor, insertion reaction of borane, radical borylation reaction, α,β-unsaturated carbonyl compound, boronate, functionalized alkyne

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Zhihao Chen, Qi Fan, Biaolin Yin, Qingjiang Li, Honggen Wang. Progress in the Syntheses of α-Boryl Carbonyl Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1706-1712.

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Fig. & Tab. 15

Scheme 1. Stability difference between two isomers

Scheme 2. Copper-catalyzed asymmetric B—H bond insertion of diazo compounds into boranes

Scheme 3. Rhodium-catalyzed B—H bond insertion of diazo compounds into boranes

Scheme 4. B—H bond insertion reactions of diazo compounds into NHC-borane using other methods

Scheme 5. B—H insertion reaction using sulfoxonium ylides/ terminal alkynes as carbene precursors

Scheme 6. Radical-mediated α-borylation reaction of α,β-un- saturated carbonyl compounds

Scheme 7. Radical-mediated borylation of alkenyl triflates

Scheme 8. Photoredox radical defluoroborylation/arylborylation reaction

Scheme 9. Photo-induced sulfur radical-catalyzed α-borylation reaction

Scheme 10. I2-catalyzed α-borylation reaction of α,β-unsatu- rated esters

Scheme 11. Boryl-migrative ring-opening reaction of epoxy vinyl boronates

Scheme 12. Wacker oxidation reaction of alkenylboronates

Scheme 13. Synthesis of α-boryl-ketones via oxidative difunctionalization reaction

Scheme 14. Synthesis of α-boryl-ketones from alkynyl boronates

Scheme 15. Synthesis of α-boryl-ketones via oxidative/hydra- tion reactions

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α-硼取代羰基类化合物的合成进展

Progress in the Syntheses of α-Boryl Carbonyl Compounds

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