分子筛负载铜水相催化α,β-不饱和化合物的共轭硼化反应

doi:10.6023/cjoc202011017

有机化学 ›› 2021, Vol. 41 ›› Issue (5): 2074-2081.DOI: 10.6023/cjoc202011017 上一篇下一篇

研究论文

分子筛负载铜水相催化α,β-不饱和化合物的共轭硼化反应

严沣^a^,^b, 周丽洁^a^,^b, 韩彪^a^,^b, 张瑶瑶^a^,^*(), 李博解^a^,^*(), 汪连生^a, 朱磊^a^,^b^,^c^,^*()

a 湖北工程学院化学与材料科学学院湖北孝感 432000
b 湖北大学材料科学与工程学院武汉 430062
c 华中科技大学生物无机化学与药物湖北省重点实验室武汉 430074

收稿日期:2020-11-11 修回日期:2020-11-17 发布日期:2021-02-22
通讯作者: 张瑶瑶, 李博解, 朱磊
基金资助:
国家自然科学基金(21774029); 湖北省自然科学基金(2019CFB237); 湖北省自然科学基金(2019CFB354); 湖北省高等学校优秀中青年科技创新团队计划项目(T201816); 孝感市自然科学计划(XGKJ201910047); 孝感市自然科学计划(XGKJ2020010053); 湖北省“楚天学者”计划; 湖北工程学院高水平硕士学位论文培育资助项目

Zeolite Immobilized Copper Catalyzed Conjugate Borylation of α,β-Unsaturated Compounds in Aqueous Media

Feng Yan^a^,^b, Lijie Zhou^a^,^b, Biao Han^a^,^b, Yaoyao Zhang^a^,^*(), Bojie Li^a^,^*(), Liansheng Wang^a, Lei Zhu^a^,^b^,^c^,^*()

a School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan, Hubei 432000
b School of Materials Science and Engineering, Hubei University, Wuhan 430062
c Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, Huazhong University of Science and Technology, Wuhan 430074

Received:2020-11-11 Revised:2020-11-17 Published:2021-02-22
Contact: Yaoyao Zhang, Bojie Li, Lei Zhu
About author:
* Corresponding authors. E-mail: lei.zhu@hbeu.edu.cn;
E-mail: yaoyaozhang@hbeu.edu.cn;
E-mail: bojie.li@hbeu.edu.cn
Supported by:
National Natural Science Foundation of China(21774029); Natural Science Foundation of Hubei Province(2019CFB237); Natural Science Foundation of Hubei Province(2019CFB354); Young and Middle-Aged Science and Technology Innovation Team Project in Higher Education Institutions of Hubei Province(T201816); Natural Science Foundation of Xiaogan City(XGKJ201910047); Natural Science Foundation of Xiaogan City(XGKJ2020010053); Chutian Scholar" Program of Hubei Province; High-Level Master's Thesis Cultivation Project of Hubei Engineering University

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摘要/Abstract

有机硼化物是一类重要的有机合成中间体. 以分子筛负载铜为催化剂, 在水相中温和的条件下, 实现α,β-不饱和化合物的共轭硼化反应, 建立了一种制备β-硼取代化合物的直接有效的新方法. 该方法操作简单, 底物普适性好, 可适用于不同类型取代的底物, 均以较高收率得到目标产物. 催化剂在反应结束后可通过离心分离回收, 循环使用7次后依然保持较高的催化反应活性.

关键词: 分子筛负载铜, α,β-不饱和化合物, 水相, 回收再利用

An eco-friendly zeolite immobilized copper catalyzed cojugate borylation of α,β-unsaturated compounds which was accomplished in aqueous media under mild conditions was reported. This method provided a direct and efficient pathway to achieve an important class of β-borylated compounds. Desired products were obtained in good to excellent yields with broad substrate scope. The advantages of this newly developed method include operational simplicity, mild conditions, good functional group tolerance and recyclability of catalyst. Remarkably, this zeolite supported copper catalyst could be recovered easily by simple centrifugation and reused for seven times without any significant decrease of catalytic activity.

Key words: zeolite immobilized copper, α,β-unsaturated compound, aqueous media, recycle and reuse

引用此文

严沣, 周丽洁, 韩彪, 张瑶瑶, 李博解, 汪连生, 朱磊. 分子筛负载铜水相催化α,β-不饱和化合物的共轭硼化反应[J]. 有机化学, 2021, 41(5): 2074-2081.

Feng Yan, Lijie Zhou, Biao Han, Yaoyao Zhang, Bojie Li, Liansheng Wang, Lei Zhu. Zeolite Immobilized Copper Catalyzed Conjugate Borylation of α,β-Unsaturated Compounds in Aqueous Media[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2074-2081.

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图/表 7

Figure 1. Biological compounds containing boron functional groups

Entry	Catalyst	Solvent (V:V)	Yield^b/%
1	Zeolite-Cu	Tolunene	NR^c
2	Zeolite-Cu	Et₂O	NR^c
3	Zeolite-Cu	THF	Trace
4	Zeolite-Cu	EtOH	69
5	Zeolite-Cu	MeOH	71
6	Zeolite-Cu	H₂O	37
7^d	Zeolite-Cu	H₂O	48
8	Zeolite-Cu	THF/H₂O (1:3)	77
9	Zeolite-Cu	THF/H₂O (3:1)	66
10	Zeolite-Cu	THF/H₂O (1:1)	97
11^e	Zeolite-Cu	THF/H₂O (1:1)	84
12	Zeolite+CuCl₂?2H₂O	THF/H₂O (1:1)	42
13	—	THF/H₂O (1:1)	NR^c
14^f	Zeolite-Cu	THF/H₂O (1:1)	95

Table 1. Optimization of reaction conditionsa

Table 1. Substrate scope of α,β-unsaturated acceptors a,b

Scheme 1. Gram scale synthesis of 3m and 3f

Figure 2. Centrifugation of the reaction mixture obtained from the reaction of chalcone 2a with B2pin2 1

Figure 3. Recycle and reuse of Zeolite-Cu catalyst

Scheme 2. Plausible mechanism

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分子筛负载铜水相催化α,β-不饱和化合物的共轭硼化反应

Zeolite Immobilized Copper Catalyzed Conjugate Borylation of α,β-Unsaturated Compounds in Aqueous Media

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