Graphene-derived Materials for Metal-free Carbocatalysis of Organic Reactions

doi:10.6023/A21070340

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (11): 1360-1371.DOI: 10.6023/A21070340 Previous Articles Next Articles

Review

石墨烯衍生物作为无金属碳基催化剂在有机催化中的应用

黄杰, 奚江波^*(), 陈伟^*(), 柏正武

武汉工程大学化学与环境工程学院绿色化工过程教育部重点实验室武汉 430205

投稿日期:2021-07-23 发布日期:2021-08-23
通讯作者: 奚江波, 陈伟

作者简介:

黄杰, 2019年本科毕业于武汉工程大学, 目前在武汉工程大学化学与环境工程学院柏正武课题组开展研究工作, 研究方向是碳基催化剂在有机反应中的应用.

奚江波, 博士、副教授、硕士生导师. 主要研究领域涉及高性能贵金属纳米催化剂、单原子催化剂和无金属碳基催化剂的制备及其在有机催化、电催化、生物传感等方面的应用, 以及催化机理的研究. 近年来在Advanced Functional Materials、Applied Catalysis B: Environmental、Journal of Catalysis等国际期刊上发表了学术论文30余篇, 获授权中国发明专利5项.

陈伟, 博士, 副教授, 硕士生导师. 主要研究领域涉及无机材料的合成、表征与应用, 并从事手性分离材料的研究及色谱分析工作. 主持湖北省教育厅科学技术研究计划重点项目1项, 在国内外学术期刊上发表科研论文20余篇, 其中SCI收录论文7篇, 授权发明专利1项.

柏正武, 博士、教授、博士生导师. 研究领域涉及有机合成、药物研制及手性功能材料的制备与应用. 主持并完成了4项国家自然科学基金资助的面上项目, 取得了一些有自主知识产权的研究成果, 获得多项发明专利权, 在国际学术期刊上发表研究论文60余篇.

基金资助:
国家自然科学基金(51772110); 绿色化工过程教育部重点实验室开放基金(GCP20200205)

Graphene-derived Materials for Metal-free Carbocatalysis of Organic Reactions

Jie Huang, Jiangbo Xi(), Wei Chen(), Zhengwu Bai

School of Chemistry and Environmental Engineering, Key Laboratory of Green Chemical Engineering Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430205, China

Received:2021-07-23 Published:2021-08-23
Contact: Jiangbo Xi, Wei Chen
Supported by:
National Natural Science Foundation of China(51772110); Open Project of Key Laboratory of Green Chemical Engineering Process of Ministry of Education(GCP20200205)

The rise in global demand for green chemistry and sustainable development have driven immense research in the fundamental science of catalysis. Metal-free catalysis, serves as an ideal industrial technology, has emerged as a new frontier and hot point in modern catalysis science due to its green and sustainable properties. As a new carbonaceous material, graphene exhibits high surface area, excellent stability, unique mechanical and electronic properties. Its physical and chemical properties can be further modulated by modification and functionalization. Graphene derivatives have been successfully employed in a variety of chemical transformations recently, showing them to be promising metal-free organocatalysts. This review highlights the recent advancements of graphene-derived materials as metal-free carbocatalysts and their application in organic reactions, such as oxidation, reduction or hydrogenation, coupling, substitution, etc. The possible structure-performance relationships of graphene-based carbocatalysts and metal-free organocatalytic mechanisms are also emphasized.

Key words: graphene, graphene-derived material, carbocatalyst, organic reaction, metal-free catalysis, catalytic mechanism

Cite this article

Jie Huang, Jiangbo Xi, Wei Chen, Zhengwu Bai. Graphene-derived Materials for Metal-free Carbocatalysis of Organic Reactions[J]. Acta Chimica Sinica, 2021, 79(11): 1360-1371.

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Catalyst	Preparation method	Functional groups or dopants	Reaction
GO^[66]	Hummers method	O-containing groups	Oxidation of alcohol
abGO^[68]	GO was treated with sequential base and acid	O-containing groups
NG-T^[69]	GO annealed under NH₃ flow	Doped N atoms
BG^[70]	GO annealed with boric acid	Doped B atoms (2.9%)
G1000^[71]	Pyrolysis of the sulfate lignin	Doped S and O atoms
CCG^[55]	Chemical reduction of GO	π-system of graphene	Oxidation of benzene
GO^[72]	Modified Hummers method	O-containing groups	Oxidation of cyclohexane
NGO^[73]	Modified Hummers method	O-containing groups	Oxidation of alkyl-substituted arenes
LC-N^[74]	CVD method with acetonitrile as N source	Doped N atoms (8.9%)	Oxidation of alkyl-substituted arenes
NG^[75]	Arc-discharge exfoliation and subsequently annealed with NH₃	Doped N atoms (0.42%)	Oxidation of olefin
rGO^[76]	GO reduction (modified Wallace's method)	The zigzag edges of rGO	Reduction of nitroaromatics
NG^[77]	Hydrothermal treatment of GO-urea mixture and subsequent annealing	Doped N atoms (2.03%)
NHG^[78]	Hydrothermal treatment of GO-NH₃-H₂O₂mixture	Doped N atoms(9.77%)
NPG^[79]	Pyrolysis of a microwave-exfoliated graphite and hexachlorocyclotriphosphazene	Doped N and P atoms
Graphene^[80]	Pyrolysis of alginate	Lewis acid-base pairs	Selective acetylene hydrogenation
GO^[81]	Modified Hummers method	O-containing groups	Cross-coupling reaction
GO^[82]	—	O-containing groups	Cross-coupling reaction
Graphite oxide^[83]	Modified Hummers method	O-containing groups	Oxidative coupling of amines
ba-GO^[84]	GO was treated with base and acid	O-containing groups
PG^[85]	Annealing of triphenylphosphine	Doped P atoms
BNHG^[62]	Annealing of of dicyandiamide, glucose and boric acid	Doped B and N atoms
GO^[86]	Modified Hummers method	O-containing groups	Friedel-Crafts alkylation
GO^[87]	Modified Hummers method	O-containing groups
GO^[88]	Hummers method	O-containing groups
Graphite^[89]	—	—	Friedel-Crafts acylation
GR-SO₃H^[90]	rGO reacts with sodium nitrite and sulfanilic acid at room temperature	Denzenesulfonic acid groups	Transesterification
GO-S^[91]	Modified Hummers method	Sulfonic acid groups and O-containing groups	Esterification
Graphite oxide^[92]	Hummers method	—	Claisen-Schmidt condensation
GO-DETA^[93]	GO modification with triethylamine	Primary, secondary amino and Oxygen-containing groups	Michael reaction and Knoevenagel reaction
GO^[94]	Modified Hummers method	Oxygen-containing groups	Hydrolysis reaction
GO^[95]	—	O-containing groups	N-formylation reaction
GO^[96]	—	O-containing groups	Dehydrogenation reaction
GO^[97]	—	O-containing groups	Iodization reaction
Graphite oxide^[98]	Hummers method	O-containing groups	Dehydration reaction
Graphite^[99]	—	—	Dehydration reaction

Catalyst	Preparation method	Functional groups or dopants	Reaction
GO^[66]	Hummers method	O-containing groups	Oxidation of alcohol
abGO^[68]	GO was treated with sequential base and acid	O-containing groups
NG-T^[69]	GO annealed under NH₃ flow	Doped N atoms
BG^[70]	GO annealed with boric acid	Doped B atoms (2.9%)
G1000^[71]	Pyrolysis of the sulfate lignin	Doped S and O atoms
CCG^[55]	Chemical reduction of GO	π-system of graphene	Oxidation of benzene
GO^[72]	Modified Hummers method	O-containing groups	Oxidation of cyclohexane
NGO^[73]	Modified Hummers method	O-containing groups	Oxidation of alkyl-substituted arenes
LC-N^[74]	CVD method with acetonitrile as N source	Doped N atoms (8.9%)	Oxidation of alkyl-substituted arenes
NG^[75]	Arc-discharge exfoliation and subsequently annealed with NH₃	Doped N atoms (0.42%)	Oxidation of olefin
rGO^[76]	GO reduction (modified Wallace's method)	The zigzag edges of rGO	Reduction of nitroaromatics
NG^[77]	Hydrothermal treatment of GO-urea mixture and subsequent annealing	Doped N atoms (2.03%)
NHG^[78]	Hydrothermal treatment of GO-NH₃-H₂O₂mixture	Doped N atoms(9.77%)
NPG^[79]	Pyrolysis of a microwave-exfoliated graphite and hexachlorocyclotriphosphazene	Doped N and P atoms
Graphene^[80]	Pyrolysis of alginate	Lewis acid-base pairs	Selective acetylene hydrogenation
GO^[81]	Modified Hummers method	O-containing groups	Cross-coupling reaction
GO^[82]	—	O-containing groups	Cross-coupling reaction
Graphite oxide^[83]	Modified Hummers method	O-containing groups	Oxidative coupling of amines
ba-GO^[84]	GO was treated with base and acid	O-containing groups
PG^[85]	Annealing of triphenylphosphine	Doped P atoms
BNHG^[62]	Annealing of of dicyandiamide, glucose and boric acid	Doped B and N atoms
GO^[86]	Modified Hummers method	O-containing groups	Friedel-Crafts alkylation
GO^[87]	Modified Hummers method	O-containing groups
GO^[88]	Hummers method	O-containing groups
Graphite^[89]	—	—	Friedel-Crafts acylation
GR-SO₃H^[90]	rGO reacts with sodium nitrite and sulfanilic acid at room temperature	Denzenesulfonic acid groups	Transesterification
GO-S^[91]	Modified Hummers method	Sulfonic acid groups and O-containing groups	Esterification
Graphite oxide^[92]	Hummers method	—	Claisen-Schmidt condensation
GO-DETA^[93]	GO modification with triethylamine	Primary, secondary amino and Oxygen-containing groups	Michael reaction and Knoevenagel reaction
GO^[94]	Modified Hummers method	Oxygen-containing groups	Hydrolysis reaction
GO^[95]	—	O-containing groups	N-formylation reaction
GO^[96]	—	O-containing groups	Dehydrogenation reaction
GO^[97]	—	O-containing groups	Iodization reaction
Graphite oxide^[98]	Hummers method	O-containing groups	Dehydration reaction
Graphite^[99]	—	—	Dehydration reaction

Reaction	Catalyst	Substrate	Product	Probable active site
Oxidation of alcohol	GO^[66]	Alcohol	Ketone/aldehyde	Epoxide groups
	abGO^[68]	Benzylic alcohol	Benzaldehyde	Phenol hydroxyl groups
	NG-T^[69]	Benzylic alcohol	Benzaldehyde	Graphitic sp²-N sites
	BG^[70]	Benzylic alcohol	Benzaldehyde	B doping species (BC₃)
	G1000^[71]	Benzylic alcohol	Benzaldehyde	Doped S and O atoms
Oxidation of benzene	CCG^[55]	Benzene	Phenol	π-system of graphene and O-containing groups
Oxidation of cyclohexane	GO^[72]	Cyclohexane	Cyclohexanol Cyclohexanone Adipic acid	Carboxylic acid groups
Oxidation of alkyl- substituted arenes	NGO^[73]	Toluene	Benzoic acid	—
Oxidation of alkyl- substituted arenes	LC-N^[74]	Ethylbenzene	Acetophenone	C atoms adjacent to N atoms
Oxidation of olefin	NG^[75]	Olefin	Alkylene oxide	Graphite N
Reduction of nitroaromatics	rGO^[76]	Nitrobenzene	Aniline	Edge sites
Reduction of nitroaromatics	NG^[77]	Nitroaromatics	Aromatic amine	Graphitic N
Reaction	Catalyst	Substrate	Product	Probable active site
	NHG^[78]	Nitroaromatics	Aromatic amine	Doped N atoms
	NPG^[79]	Nitroaromatics	Aromatic amine	Doped N and P atoms
Selective hydrogenation	Graphene^[80]	Acetylene Ethylene	Ethylene Ethane	Lewis acid-base pairs
Cross-coupling reaction	GO^[81]	Iodobenzene Benzene	Biaryl compounds	O-containing groups
Cross-coupling reaction	GO^[82]	1,3,5-Trimethoxy-benzene	Biaryl compounds	O-containing group, π-conjugated system and unpaired electrons
Oxidative coupling of amines	Graphite oxide^[83]	Benzylamine	N-Benzylidene aniline	—
	ba-GO^[84]	Benzylamine	N-Benzylidene aniline	The edge sites carboxyl
	PG^[85]	Benzylamine	N-Benzylidene aniline	Doped of P atoms
	BNHG^[62]	Benzylamine	N-Benzylidene aniline	Doped B and N atoms
Friedel-Crafts alkylation	GO^[86]	Aromatics Styrene Alcohol	Diarylalkane	O-containing groups
	GO^[87]	Aldehydes Indoles	Bis(indolyl)methanes	O-containing groups
	GO^[88]	Indole Ethers	3,3'-Bisindolylmethane	—
Friedel-Crafts acylation	Graphite^[89]	Aromatic compounds	Acylated products	—
Transesterification	GR-SO₃H^[90]	Palm oil	Biodiesel	Benzenesulfonic acid groups
Esterification	GO-S^[91]	Oleic acid	Biodiesel	Sulfonic acid groups and carboxylic acid groups
Claisen-Schmidt Condensation	Graphite oxide^[92]	Phenylacetylene Benzyl alcohol	Chalcone	—
Michael reaction Knoevenagel reaction	GO-DETA^[93]	Benzaldehyde Malononitrile (E)-Chalcone	Benzylidenemalononitrile 2-(3-oxo-1,3-diphenylpropyl)malononitrile	Primary, secondary amino and carboxyl groups
Hydrolysis reaction	GO^[94]	Cellulose	Glucose	Hydroxyl and carboxyl groups
N-formylation reaction	GO^[95]	Tetrahydroisoquinoline	Formamide	Carboxylic acid group
Dehydrogenation reaction	GO^[96]	Tetrahydroisoquinoline	Dehydrogenation products	O-containing groups
Iodization reaction	GO^[97]	Benzothiazole	Iodination product	Unpaired electrons
Dehydration reaction	Graphite oxide^[98]	Benzyl alcohol	Poly(phenylene methylene)	O-containing groups
Dehydration reaction	Graphite^[99]	Ethanol Silver nitrate	Silver cyanide	—

Reaction	Catalyst	Substrate	Product	Probable active site
Oxidation of alcohol	GO^[66]	Alcohol	Ketone/aldehyde	Epoxide groups
	abGO^[68]	Benzylic alcohol	Benzaldehyde	Phenol hydroxyl groups
	NG-T^[69]	Benzylic alcohol	Benzaldehyde	Graphitic sp²-N sites
	BG^[70]	Benzylic alcohol	Benzaldehyde	B doping species (BC₃)
	G1000^[71]	Benzylic alcohol	Benzaldehyde	Doped S and O atoms
Oxidation of benzene	CCG^[55]	Benzene	Phenol	π-system of graphene and O-containing groups
Oxidation of cyclohexane	GO^[72]	Cyclohexane	Cyclohexanol Cyclohexanone Adipic acid	Carboxylic acid groups
Oxidation of alkyl- substituted arenes	NGO^[73]	Toluene	Benzoic acid	—
Oxidation of alkyl- substituted arenes	LC-N^[74]	Ethylbenzene	Acetophenone	C atoms adjacent to N atoms
Oxidation of olefin	NG^[75]	Olefin	Alkylene oxide	Graphite N
Reduction of nitroaromatics	rGO^[76]	Nitrobenzene	Aniline	Edge sites
Reduction of nitroaromatics	NG^[77]	Nitroaromatics	Aromatic amine	Graphitic N
Reaction	Catalyst	Substrate	Product	Probable active site
	NHG^[78]	Nitroaromatics	Aromatic amine	Doped N atoms
	NPG^[79]	Nitroaromatics	Aromatic amine	Doped N and P atoms
Selective hydrogenation	Graphene^[80]	Acetylene Ethylene	Ethylene Ethane	Lewis acid-base pairs
Cross-coupling reaction	GO^[81]	Iodobenzene Benzene	Biaryl compounds	O-containing groups
Cross-coupling reaction	GO^[82]	1,3,5-Trimethoxy-benzene	Biaryl compounds	O-containing group, π-conjugated system and unpaired electrons
Oxidative coupling of amines	Graphite oxide^[83]	Benzylamine	N-Benzylidene aniline	—
	ba-GO^[84]	Benzylamine	N-Benzylidene aniline	The edge sites carboxyl
	PG^[85]	Benzylamine	N-Benzylidene aniline	Doped of P atoms
	BNHG^[62]	Benzylamine	N-Benzylidene aniline	Doped B and N atoms
Friedel-Crafts alkylation	GO^[86]	Aromatics Styrene Alcohol	Diarylalkane	O-containing groups
	GO^[87]	Aldehydes Indoles	Bis(indolyl)methanes	O-containing groups
	GO^[88]	Indole Ethers	3,3'-Bisindolylmethane	—
Friedel-Crafts acylation	Graphite^[89]	Aromatic compounds	Acylated products	—
Transesterification	GR-SO₃H^[90]	Palm oil	Biodiesel	Benzenesulfonic acid groups
Esterification	GO-S^[91]	Oleic acid	Biodiesel	Sulfonic acid groups and carboxylic acid groups
Claisen-Schmidt Condensation	Graphite oxide^[92]	Phenylacetylene Benzyl alcohol	Chalcone	—
Michael reaction Knoevenagel reaction	GO-DETA^[93]	Benzaldehyde Malononitrile (E)-Chalcone	Benzylidenemalononitrile 2-(3-oxo-1,3-diphenylpropyl)malononitrile	Primary, secondary amino and carboxyl groups
Hydrolysis reaction	GO^[94]	Cellulose	Glucose	Hydroxyl and carboxyl groups
N-formylation reaction	GO^[95]	Tetrahydroisoquinoline	Formamide	Carboxylic acid group
Dehydrogenation reaction	GO^[96]	Tetrahydroisoquinoline	Dehydrogenation products	O-containing groups
Iodization reaction	GO^[97]	Benzothiazole	Iodination product	Unpaired electrons
Dehydration reaction	Graphite oxide^[98]	Benzyl alcohol	Poly(phenylene methylene)	O-containing groups
Dehydration reaction	Graphite^[99]	Ethanol Silver nitrate	Silver cyanide	—

石墨烯衍生物作为无金属碳基催化剂在有机催化中的应用

Graphene-derived Materials for Metal-free Carbocatalysis of Organic Reactions

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