1,4-氮硼杂芳环在有机和过渡金属催化中的应用

doi:10.6023/cjoc202301018

摘要/Abstract

总结了1,4-氮硼杂芳环在有机和过渡金属催化中的最新进展, 涵盖三部分内容: 一是简要介绍了1,4-氮硼杂芳环的发展历史; 二是重点介绍了1,4-氮硼杂芳环作为有机小分子催化剂在光致氧化三芳基膦中的应用; 三是详细阐述了1,4-氮硼杂芳环作为配体在钯催化的烯炔的立体选择性硼化反应中的应用. 此外, 对这一领域的未来发展进行了展望.

关键词: 1,4-氮硼杂芳环, 过渡金属, 光致氧化, 有机催化

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

引用此文

景科, 张攀科, 徐森苗. 1,4-氮硼杂芳环在有机和过渡金属催化中的应用[J]. 有机化学, 2023, 43(5): 1742-1750.

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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图/表 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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