Application of 1,4-Azaborines in Organic and Transition Metal Catalysis

doi:10.6023/cjoc202301018

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (5): 1742-1750.DOI: 10.6023/cjoc202301018 Previous Articles Next Articles

Special Issue: 有机硼化学专辑

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1,4-氮硼杂芳环在有机和过渡金属催化中的应用

景科^a^,^b, 张攀科^a^,^*(), 徐森苗^b^,^*()

a 郑州大学化学学院绿色催化中心郑州 450001
b 中国科学院兰州化学物理研究所羰基合成与选择氧化国家重点实验室兰州 730000

收稿日期:2023-01-18 修回日期:2023-02-15 发布日期:2023-03-07
通讯作者: 张攀科, 徐森苗

Application of 1,4-Azaborines in Organic and Transition Metal Catalysis

Ke Jing^a^,^b, Panke Zhang^a(), Senmiao Xu^b()

a Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000

Received:2023-01-18 Revised:2023-02-15 Published:2023-03-07
Contact: Panke Zhang, Senmiao Xu

The recent progress of 1,4-azaborines in organic and transition metal catalysis is summarized, which consists of three parts. The first part briefly describes the history of 1,4-azaborines, the second part emphasizes on the application of 1,4-azaborines as an organocatalyst in the aerobic photooxidation of triaryl phosphines, and the last part discribes the use of 1,4-azaborines as the ligand in palladium-catalyzed stereoselective borylation of enynes. The future direction of this field is also proposed.

Key words: 1,4-azaborine, transition metals, photooxidation, organocatalysis

Cite this article

Ke Jing, Panke Zhang, Senmiao Xu. Application of 1,4-Azaborines in Organic and Transition Metal Catalysis[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1742-1750.

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Fig. & Tab. 13

Scheme 1. Isomers of azaborines (A) and brief history of 1,4-azaborines (B)

Scheme 2. Selected examples for the DBAB 1-catalzyed aerobic oxidation of Ar3P

Scheme 3. Proposed mechanism for the 1-catalyzed aerobic photooxidation of Ar3P

Scheme 4. Synthesis of monobenzo-fused 1,4-azaborine and its application

Scheme 5. Synthesis of monobenzo-fused 1,4-azaborine and its phosphine ligands (Senphos)

Scheme 6. Selected examples for the trans-hydroboration of terminal 1,3-enynes 25 with Senphos 23c

Scheme 7. Selected examples for the trans-hydroboration of internal 1,3-enynes 27 with Senphos 23b

Scheme 8. Mechanism of trans-hydroboration of 28e based on DFT calculations

Scheme 9. Selected examples for the trans-cyanoboration of alkyl or terminal 1,3-enynes 30 with Senphos 29

Scheme 10. Selected examples for the trans-cyanoboration of aryl 1,3-enynes 32 with Senphos 23a

Scheme 11. Formation of carbon-bound boron enolate (A) and hypothesis for carboboration of 1,3-enynes (B)

Scheme 12. Selected examples for the reaction scope of C-boron enolates

Scheme 13. Selected examples for the reaction scope of internal 1,3-enynes

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1,4-氮硼杂芳环在有机和过渡金属催化中的应用

Application of 1,4-Azaborines in Organic and Transition Metal Catalysis

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Fig. & Tab. 13

References 32

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