联吡啶配体促进铬催化炔烃的顺式硼氢化反应

doi:10.6023/cjoc202210006

有机化学 ›› 2023, Vol. 43 ›› Issue (7): 2447-2453.DOI: 10.6023/cjoc202210006 上一篇下一篇

研究论文

联吡啶配体促进铬催化炔烃的顺式硼氢化反应

王莎, 陈常鹏, 曾小明^*()

四川大学化学学院成都 610064

收稿日期:2023-05-20 修回日期:2023-06-06 发布日期:2023-06-13
通讯作者: 曾小明
基金资助:
国家自然科学基金(21971168); 国家自然科学基金(22125107)

Bipyridine Ligand-Promoted cis-Selective Hydroboration of Alkynes with Chromium Catalysis

Sha Wang, Changpeng Chen, Xiaoming Zeng()

College of Chemistry, Sichuan University, Chengdu 610064

Received:2023-05-20 Revised:2023-06-06 Published:2023-06-13
Contact: Xiaoming Zeng
Supported by:
National Natural Science Foundation of China(21971168); National Natural Science Foundation of China(22125107)

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摘要/Abstract

报道了金属铬催化炔烃的硼氢化反应. 廉价易得的三氯化铬在4,4'-二叔丁基-2,2'-联吡啶配体及单质镁的还原作用下表现出高反应活性, 催化实现了频哪醇硼烷与炔烃加成的硼氢化反应, 为室温条件下制备烯基硼化合物提供了一条有效的合成策略.

关键词: 铬催化, 硼氢化反应

The chromium-catalyzed hydroboration of alkynes under mild conditions was reported. Low-cost chromium(III) chloride combined with 4,4'-di-tert-butyl 2,2'-bipyridine as the ligand and magnesium as the reductant shows high reactivity, which can catalyze and promote the hydroboration of alkynes with pinacolborane, thereby providing a strategy to form borylated olefins at ambient temperature.

Key words: chromium catalysis, hydroboration

引用此文

王莎, 陈常鹏, 曾小明. 联吡啶配体促进铬催化炔烃的顺式硼氢化反应[J]. 有机化学, 2023, 43(7): 2447-2453.

Sha Wang, Changpeng Chen, Xiaoming Zeng. Bipyridine Ligand-Promoted cis-Selective Hydroboration of Alkynes with Chromium Catalysis[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2447-2453.

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图/表 5

Scheme 1. Non-precious metal-catalyzed hydroboration of alkynes

Entry Deviation from standard conditions Yield/%

Table 1. Optimization of reaction parameters in the catalytic cis- selective hydroboration of alkynea

Table 2. Cr-catalyzed cis-selective hydroboration of alkynes for the synthesis of olefinated boronate esters

Scheme 2. Preliminary mechanistic studies

Scheme 3. Gram-scale hydroboration and synthetic applications

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联吡啶配体促进铬催化炔烃的顺式硼氢化反应

Bipyridine Ligand-Promoted cis-Selective Hydroboration of Alkynes with Chromium Catalysis

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