共价有机骨架在交叉偶联反应中的应用进展

doi:10.11949/0438-1157.20230636

摘要/Abstract

摘要：

交叉偶联反应是构建C—C键、C—N键和C—O键的高效方法。利用有机聚合物材料作为催化剂载体进行的异相催化反应具有催化剂可回收、反应高效等优点。综述了共价有机骨架（COFs）通过负载金属构成异相催化剂，在多种交叉偶联反应中的应用；对催化效率和催化剂的循环次数进行了详细描述，并指出了该领域面临的问题与挑战。

关键词: 催化剂, 催化剂载体, 有机化合物, 交叉偶联反应, 共价有机骨架, 异相催化

Abstract:

Cross-coupling reactions are efficient methods for building C—C bonds, C—N bonds, and C—O bonds. Heterogeneous catalytic reactions with organic polymers as catalyst supporters possess the advantages of recyclable catalysts and high efficiency. This article reviews the application of covalent organic frameworks (COFs) to form heterogeneous catalysts by loading metals in various cross-coupling reactions. The catalytic efficiency and catalyst cycle times are described in detail, and pointed out the problems and challenges in this field.

Key words: catalyst, catalyst support, organic compounds, cross-coupling reactions, covalent organic frameworks, heterogeneous catalysis

中图分类号:

TQ 028.8

唐翠曼, 刘佳琦, 杨威, 孙钟, 仉昊楠, 王兵兵, 徐小惠. 共价有机骨架在交叉偶联反应中的应用进展[J]. 化工学报, 2023, 74(11): 4397-4418.

Cuiman TANG, Jiaqi LIU, Wei YANG, Zhong SUN, Haonan ZHANG, Bingbing WANG, Xiaohui XU. Progress in the application of covalent organic frameworks in cross-coupling reactions[J]. CIESC Journal, 2023, 74(11): 4397-4418.

图/表 27

图1 COF-1与COF-5结构示意图[32]

Fig.1 Structures of COF-1 and COF-5[32]

表1 COFs催化的交叉偶联反应

Table 1 COFs catalyzed cross-coupling reactions

COFs催化剂	偶联反应	成键方式	循环次数	图示	文献
Pd/COF-LZU1	Suzuki-Miyaura	C—C	4	2	[44]
Pd/H₂P-Bph-COF	Suzuki-Miyaura	C—C	4	3	[45]
Pd(OAc)₂@COF-300	Suzuki-Miyaura	C—C	5	4	[46]
	Heck		—
	Sonogashira		—
Pd(Ⅱ)@TAT-DHBD	Suzuki-Miyaura	C—C	3	6	[47]
Pd(0)@TAT-DHBD
Pd(Ⅱ)@TAT-TFP
Pd(0)@TAT-TFP
Pd@COF-NHC	Suzuki-Miyaura	C—C	8	7	[48]
Pd NPs@Phos-COF-1	Suzuki-Miyaura	C—C	5	8	[49]
PdAu NPs@Phos-COF-1	tandem cross-coupling and hydride reduction of 1-bromo-4-nitrobenzene	C—C	—	8	[49]
HP-TpAzo@Pd	Suzuki-Miyaura	C—C	5	9	[50]
Pd NPs@TTT-COF	Suzuki-Miyaura	C—C	4	10	[51]
	Stille	C—C	—
	Heck	C—C	—
	Sonogashira	C—C	—
Pd@TPM-3D-COF-BPY	Suzuki-Miyaura	C—C	5	11	[52]
Pd(Ⅱ)@SP-3D-COF-BPY	Suzuki-Miyaura	C—C	5	12	[53]
NiCl@RIO-12	Suzuki-Miyaura	C—C	3	13	[54]
Pd/COF-SMC₂	Suzuki-Miyaura	C—C	3	14	[55]
Pd@Phen-COF	Suzuki-Miyaura	C—C	5	15	[56]
Pd@Phen-COF	Heck	C—C	5	15	[56]
Pd(0)@TpPa-1	Heck	C—C	4	16	[57]
	Sonogashira	C—C	4
	one-pot sequential Heck/Sonogashira coupling reactions	C—C	—
Pd(0)-trzn-COF	Heck	C—C	6	17	[58]
Pd(Ⅱ)@Bpy-COF	Heck	C—C	4	18	[59]
Mn/Pd@Py-2, 2′-BPyPh COF	Heck-epoxidation tandem reaction	C—C	2	19	[60]
Pd/COF-BTDH	Heck	C—C	9	21	[61]
Cu@IISERP-COF9	Glaser-Hay	C—N	5	22	[62]
Cu@MCIP-1	Chan-Lam	C—N	4	23	[63]
Cu@PI-COF	Chan-Lam	C—N	8	24	[64]
Cu@PI-COF	Chan-Lam	C—N	8	25	[65]
sp²c-COF_dpy-Ni	C—O cross-coupling reaction	C—O	4	26	[66]

图2 Pd/COF-LZU1催化的Suzuki-Miyaura偶联反应(1 Å=0.1 nm)[44]

Fig.2 Suzuki-Miyaura coupling-reactions catalyzed by Pd/COF-LZU1[44]

图3 Pd/H2P-Bph-COF催化的Suzuki-Miyaura偶联反应[45]

Fig.3 Suzuki-Miyaura coupling-reactions catalyzed by Pd/H2P-Bph-COF[45]

图4 Pd(OAc)2@COF-300催化的C—C键偶联反应[46]

Fig.4 C—C coupling-reactions catalyzed by Pd(OAc)2@COF-300[46]

图5 Pd(0)@Thio-COF催化的Suzuki-Miyaura偶联反应[68]

Fig.5 Suzuki-Miyaura coupling-reactions catalyzed by Pd(0)@Thio-COF[68]

图6 Pd(Ⅱ)/Pd(0)TAT-DHBD/TAT-TFP催化的Suzuki-Miyaura偶联反应[47]

Fig.6 Suzuki-Miyaura coupling-reactions catalyzed by Pd(Ⅱ)/Pd(0)TAT-DHBD/TAT-TFP[47]

图7 Pd@COF-NHC催化的C—C键偶联反应[48]

Fig.7 C—C coupling-reactions catalyzed by Pd@COF-NHC[48]

图8 Suzuki-Miyaura偶联反应和串联偶联-还原反应[49]

Fig.8 Suzuki-Miyaura coupling-reactions and tandem coupling-reduction reactions[49]

图9 HP-TpAzo@Pd催化的Suzuki-Miyaura偶联反应[50]

Fig.9 Suzuki-Miyaura reactions catalyzed by HP-TpAzo@Pd[50]

图10 Pd NPs@TTT-COF催化的C—C偶联反应[51]

Fig.10 Pd NPs@TTT-COF catalyzed C—C coupling-reactions[51]

图11 Pd@TPM-3D-COF-BPY催化的Suzuki-Miyaura偶联反应[52]

Fig.11 Pd@TPM-3D-COF-BPY catalyzed Suzuki-Miyaura coupling-reactions[52]

图12 Pd(Ⅱ)@SP-3D-COF-BPY催化的Suzuki-Miyaura偶联反应[53]

Fig.12 Pd(Ⅱ)@SP-3D-COF-BPY catalyzed Suzuki-Miyaura coupling-reactions[53]

图13 NiCl@RIO-12催化的Suzuki-Miyaura偶联反应[54]

Fig.13 NiCl@RIO-12 catalyzed Suzuki-Miyaura coupling-reactions[54]

图14 Pd/COF-SMC2催化的Suzuki-Miyaura偶联反应[55]

Fig.14 Suzuki-Miyaura coupling-reactions catalyzed by Pd/COF-SMC2[55]

图15 Pd@Phen-COF催化的Suzuki-Miyaura和Mizoroki-Heck反应[56]

Fig.15 Pd@Phen-COF catalyzed Suzuki-Miyaura and Mizoroki-Heck reactions[56]

图16 Pd@TpPa-1催化的C—C偶联反应[57]

Fig.16 C—C coupling-reactions catalyzed by Pd@TpPa-1[57]

图17 Pd-trzn-COF催化的多重Heck偶联反应[58]

Fig.17 List of multi-fold Heck coupling-reactions catalyzed by Pd-trzn-COF[58]

图18 Pd(Ⅱ)@75% Bpy-COF催化的Heck偶联反应[59]

Fig.18 Heck coupling-reactions catalyzed by Pd(Ⅱ)@75% Bpy-COF[59]

图19 Mn/Pd@Py-2, 2′-BPyPh COF催化的Heck-环氧化串联反应[60]

Fig.19 Heck-epoxidation tandem reactions catalyzed by Mn/Pd@Py-2, 2′-BPyPh COF[60]

图20 Pd@CCOF-MPC催化的不对称Heck偶联-还原反应[69]

Fig.20 Asymmetric Heck coupling-reduction reactions catalyzed by Pd@CCOF-MPC[69]

图21 Pd/COF-BTDH催化的Heck偶联反应[61]

Fig.21 Heck coupling-reactions catalyzed by Pd/COF-BTDH[61]

图22 Cu@COF催化的Glaser-Hay偶联反应[62]

Fig.22 Glaser-Hay coupling-reactions catalyzed by Cu@COF[62]

图23 Cu@MCIP-1催化的Chan-Lam偶联反应[63]

Fig.23 The Chan-Lam coupling-reactions catalyzed by Cu@MCIP-1[63]

图24 Cu@PI-COF催化的Chan-Lam偶联反应[64]

Fig.24 Chan-Lam coupling-reactions catalyzed by Cu@PI-COF[64]

图25 Cu(OAc)2@PI-COF催化的Chan-Lam偶联反应[65]

Fig.25 Chan-Lam coupling-reactions catalyzed by Cu(OAc)2@PI-COF[65]

图26 sp2c-COFdpy-Ni催化的C—O偶联反应[66]

Fig.26 C—O coupling-reactions catalyzed by sp2c-COFdpy-Ni[66]

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