一种用于光催化C(sp2)‒H键官能团化通用的非均相钒酸铋催化剂

doi:10.1016/S1872-2067(23)64391-8

催化学报 ›› 2023, Vol. 46: 157-166.DOI: 10.1016/S1872-2067(23)64391-8

一种用于光催化C(sp²)‒H键官能团化通用的非均相钒酸铋催化剂

曾繁林, 朱虎林, 王茹楠, 袁晓亚, 孙凯, 屈凌波, 陈晓岚^*(), 於兵^*()

郑州大学化学学院, 绿色催化中心, 河南郑州 450001

收稿日期:2022-09-14 接受日期:2022-12-14 出版日期:2023-03-18 发布日期:2023-02-21
通讯作者: *电子信箱: chenxl@zzu.edu.cn (陈晓岚),bingyu@zzu.edu.cn (於兵)
基金资助:
国家自然科学基金(21971224);国家自然科学基金(22071222);国家自然科学基金(22171249);河南省高校重点科研项目(21A150053);河南省自然科学基金(202300410375)

Bismuth vanadate: A versatile heterogeneous catalyst for photocatalytic functionalization of C(sp²)-H bonds

Fan-Lin Zeng, Hu-Lin Zhu, Ru-Nan Wang, Xiao-Ya Yuan, Kai Sun, Ling-Bo Qu, Xiao-Lan Chen^*(), Bing Yu^*()

Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China

Received:2022-09-14 Accepted:2022-12-14 Online:2023-03-18 Published:2023-02-21
Contact: *E-mail: chenxl@zzu.edu.cn (X. Chen), bingyu@zzu.edu.cn (B. Yu)
Supported by:
National Natural Science Foundation of China(21971224);National Natural Science Foundation of China(22071222);National Natural Science Foundation of China(22171249);The Key Research Projects of Universities in Henan Province(21A150053);The Natural Science Foundation of Henan Province(202300410375)

摘要/Abstract

摘要：

近年来, 可见光诱导的有机反应条件温和、效率高, 因而备受关注. 由于多数有机物不能直接吸收可见光, 因此需要添加具有光学活性的化合物作为光催化剂, 促进反应发生. 目前有机化学工作者已经发展了许多高效的光催化剂, 如过渡金属(钌、铱等)配合物、有机染料等. 然而这些光催化剂也存在一些局限, 例如贵金属光催化剂价格昂贵, 有机染料稳定性相对较差, 而且大多数是均相催化剂, 且反应后无法回收利用. 从绿色化学的角度讲, 针对光催化的有机反应, 发展低成本、多功能、高效、可回收的非均相光催化剂具有重要意义.

本文采用水热/煅烧相结合的方法合成了三种钒酸铋晶体, 并通过粉末单晶衍射、紫外可见光吸收光谱、光电流实验、荧光发射光谱、扫描电镜等手段进行表征. 结果表明, 合成的钒酸铋属于单斜晶系, 且表现出一定的光电性能. 相较于市售的钒酸铋, 合成的BiVO₄-180具有更小的粒径, 呈现规则的椭圆形, 在模型反应中表现出更高的光催化活性. 以BiVO₄-180为非均相光催化剂, 用于多种C(sp²)‒H官能团化反应, 实现了一系列复杂有机分子的合成和药物分子米非司酮、醋酸乌利司他的后修饰. 主要涉及的有机光反应包括: N,N-二甲基芳香胺与马来酰亚胺或苄烯丙二腈的[4+2]环化反应, 吲哚C-3位、α-氨基酸酯、芳烃等化合物的直接官能团化反应. 此外, 光催化剂的回收实验表明BiVO₄-180在反应后很容易回收再利用, 在经过8次催化使用后, 其结构和催化活性几乎未发生变化. 反应机理研究表明, BiVO₄-180的光生电子和氧空位在上述有机光反应中起到关键作用.

综上, BiVO₄-180作为廉价易得、稳定的非均相光催化剂, 可以有效地应用在多种可见光催化的C(sp²)‒H官能团化反应中. 该策略具有反应条件温和, 催化剂易制备且可回收, 适用于药物修饰, 底物适用性广等优点.

关键词: 钒酸铋, 光催化, 非均相催化剂, 碳氢键官能团化, 自由基化学

Abstract:

Bismuth vanadate hydrothermally synthesized at 180 °C and then calcined (BiVO₄-180) is a versatile and stable heterogeneous photocatalyst for the functionalization of diverse C(sp²)-H bonds under ambient visible-light conditions, with a series of functionalized compounds, including tetrahydroquinoline-succinimide-fused heterocycles, tetrahydroquinolines, 3-(p-(N,N-dimethyl)ben- zyl)indoles, α-aryl α-amino acid esters, and thiocyanated/vulcanized/selenated (hetero)aromatics, synthesized in good yields (79 examples, including modified drugs and dipeptide esters). BiVO₄ photocatalysts are advantageous because they are recyclable, inexpensive, air-tolerant, and highly efficient, which are typical characteristics required to overcome the shortcomings of homogeneous photocatalysts.

Key words: Bismuth vanadate, Photocatalysis, Heterogeneous photocatalyst, C-H functionalization, Radical chemistry

曾繁林, 朱虎林, 王茹楠, 袁晓亚, 孙凯, 屈凌波, 陈晓岚, 於兵. 一种用于光催化C(sp²)‒H键官能团化通用的非均相钒酸铋催化剂[J]. 催化学报, 2023, 46: 157-166.

Fan-Lin Zeng, Hu-Lin Zhu, Ru-Nan Wang, Xiao-Ya Yuan, Kai Sun, Ling-Bo Qu, Xiao-Lan Chen, Bing Yu. Bismuth vanadate: A versatile heterogeneous catalyst for photocatalytic functionalization of C(sp²)-H bonds[J]. Chinese Journal of Catalysis, 2023, 46: 157-166.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(23)64391-8

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图/表 6

Scheme 1. BiVO4-photocatalyzed syntheses of aromatic/polyheterocyclic derivatives.

Scheme 2. Combined hydrothermal/calcination method used to prepare BiVO4.

Fig. 1. (a) XRD patterns of monoclinic scheelite BiVO4 (JCPDS 14-0688) and BiVO4-140/160/180. The diffraction peaks at 2θ values of 18.67°, 18.99°, 28.95°, 30.55°, 34.50°, 35.22°, 39.78°, 42.46°, 45.59°, 46.71°, 50.31°, 53.31°, 58.53°, and 59.26° are indexed to the (110), (011), (121), (040), (200), (002), (211), (051), (231), (240), (202), (161), (321), and (123) crystal planes of monoclinic BiVO4. (b) UV/Vis absorption spectra of BiVO4-140/160/180 and corresponding Tauc plots (insets). The lowest bandgap (2.4 eV) was calculated from each UV/Vis absorbance spectrum. (c) Transient photocurrents of BiVO4-140/160/180. (d) PL spectra of BiVO4-140/160/180 (λex = 320 nm). (e) Size distributions of BiVO4-140/160/180 and commercial BiVO4 determined by DLS using BiVO4 dispersed in 2-MeTHF (0.025 mol/L). (f?i). SEM images of BiVO4-140/160/180 and commercial BiVO4.

Scheme 3. Exploring the BiVO4-180 photocatalysis strategy for an expanded substrate range.

Scheme 4. Photocatalytic regioselective functionalizations of (hetero)aromatics using BiVO4-180.

Scheme 5. Control experiments designed to support to the proposed mechanism.

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一种用于光催化C(sp²)‒H键官能团化通用的非均相钒酸铋催化剂

Bismuth vanadate: A versatile heterogeneous catalyst for photocatalytic functionalization of C(sp²)-H bonds

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