Formal C-H/C-I Metathesis: Site-Selective C-H Iodination of 2-Aryl Benzoic Acid Derivatives Using Aryl Iodide

被引:10
作者
Gao, Zezhong [1 ,2 ]
Wang, Hang [2 ]
Zhou, Chunlin [2 ]
Wang, Ning [2 ]
Li, Shangda [2 ]
Li, Gang [2 ,3 ]
机构
[1] Fuzhou Univ, Coll Chem, Fuzhou 350002, Fujian, Peoples R China
[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China
[3] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Shanghai 200240, Peoples R China
关键词
CATALYZED ORTHO-HALOGENATION; REDUCTIVE ELIMINATION; CARBOXYLIC-ACIDS; FUNCTIONALIZATION; BONDS; HALIDES; CYCLIZATION; CLEAVAGE; EXCHANGE; ARENE;
D O I
10.1021/acs.orglett.2c01224
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-H functionalization via functional group metathesis is extremely rare. A protocol of remote site-selective C-H iodination of 2-aryl benzoic acid derivatives via formal C(sp(2))-H/C(sp(2))-I metathesis using readily available 1-iodo-4-methoxy-2-nitrobenzene as the mild iodinating reagent was reported herein. A range of 2-aryl benzoic acid derivatives including 2-(naphthalen-1-yl)benzoic acids and [1,1'-binaphthalene]-2-carboxylic acids were iodinated under mild conditions to give valuable iodinated products in a site- and chemo-selective fashion.
引用
收藏
页码:3926 / 3931
页数:6
相关论文
共 50 条
[41]   Redox-Neutral Site-Selective C-H Allylation and Iodolactonization of Benzoic Acids Using Morita-Baylis-Hillman Adducts in Water [J].
Bhattacharyya, Hemanga ;
Saha, Sharajit ;
Verma, Kshitiz ;
Punniyamurthy, Tharmalingam .
ORGANIC LETTERS, 2023, 25 (37) :6830-6834
[42]   2,2′-Biaryldicarboxylate Synthesis via Electrocatalytic Dehydrogenative C-H/C-H Coupling of Benzoic Acids [J].
Zeng, Zhongyi ;
Goebel, Jonas F. ;
Liu, Xianming ;
Goossen, Lukas J. .
ACS CATALYSIS, 2021, 11 (11) :6626-6632
[43]   Modular C-H Functionalization Cascade of Aryl Iodides [J].
Shi, Hang ;
Babinski, David J. ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (11) :3775-3778
[44]   Site-selective C-H bond carbonylation with CO2 and cobalt-catalysis [J].
Barsu, Nagaraju ;
Kalsi, Deepti ;
Sundararaju, Basker .
CATALYSIS SCIENCE & TECHNOLOGY, 2018, 8 (22) :5963-5969
[45]   Trifunctionalization of aryl iodides via intermolecular C-H acylation/intramolecular C-H alkylation achieved using palladium/norbornene cooperative catalysis [J].
Wang, Jing ;
Li, Linqiang ;
Wang, Zihan ;
Liu, Jingjing ;
Luan, Xinjun .
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (15) :4003-4008
[46]   Cu-Catalyzed Aryl C-H Halogenation Using N-Halosuccinimides via Assistance of Benzoic Acid [J].
Du Zhijun ;
Gao Lianxun ;
Lin Yingjie .
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2015, 31 (02) :167-170
[47]   Bioinspired Synthesis of Pinoxaden Metabolites Using a Site-Selective C-H Oxidation Strategy [J].
Tyagi, Sameer ;
McKillican, Bruce P. ;
Salvador, Tolani K. ;
Gichinga, Moses G. ;
Eberle, William J. ;
Viner, Russell ;
Makaravage, Katarina J. ;
Johnson, Trey S. ;
Russell, C. Adam ;
Roy, Subho .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) :6202-6211
[48]   Iron-mediated site-selective oxidative C-H/C-H cross-coupling of aryl radicals with quinones: synthesis of β-secretase-1 inhibitor B and related arylated quinones [J].
Krishna, Adarsh T. P. ;
Pandaram, Sakthivel ;
Ilangovan, Andivelu .
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (18) :3244-3251
[49]   Copper-Mediated Sequential Cyanation of Aryl C-B and Arene C-H Bonds Using Ammonium Iodide and DMF [J].
Kim, Jinho ;
Choi, Jiho ;
Shin, Kwangmin ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) :2528-2531
[50]   Palladium-Catalyzed Distal C-H Selenylation of 2-Aryl Acetamides with Diselenides and Selenyl Chlorides [J].
He, Meicui ;
Gu, Linghui ;
Tan, Yuqiang ;
Wang, Yang ;
Wang, Yuchi ;
Zhang, Chunran ;
Ma, Wenbo .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (24) :5708-5715