Progress in the application of covalent organic frameworks in cross-coupling reactions

doi:10.11949/0438-1157.20230636

Abstract

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

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

CLC Number:

TQ 028.8

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.

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.

Figures/Tables 27

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

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]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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