Recent Progress in meta-/para-Selective Aromatic C-H Borylation

被引:2
作者
Jiang Wang [1 ,2 ]
Shi Zhuangzhi [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China
[2] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225000, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
meta selectivity; para selectivity; iridium catalysis; C-H borylation; directing groups; ACTIVATION; LIGAND;
D O I
10.6023/cjoc202302022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Organoboron compounds are important building blocks to create molecular diversity. Strategies that can transform the readily available hydrocarbons into these compounds by C-H borylation are highly attractive. In this context, significant progress has been made towards iridium-catalyzed C-H borylation. Because substituted arenes typically contain ortho-, meta- and para-C-H bonds, regiocontrol has been a long-standing challenge within this type of chemistry. During the past decade, significant progress has been made in the ortho-selective C-H borylation, while the meta-/para-selectivity is still challenging. This review aims to provide a comprehensive overview of this topic on meta-/para-selective aromatic C-H borylation by iridium catalysis. This topic is categorized into directed and non-directed C-H borylation.
引用
收藏
页码:1691 / 1705
页数:15
相关论文
共 35 条
[1]   Para-Selective, Iridium-Catalyzed C-H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions [J].
Bastidas, Jose R. Montero ;
Oleskey, Thomas J. ;
Miller, Susanne L. ;
Smith, Milton R., III ;
Maleczka, Robert E., Jr. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (39) :15483-15487
[2]   Amide Effects in C-H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides [J].
Bisht, Ranjana ;
Hoque, Md Emdadul ;
Chattopadhyay, Buddhadeb .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (48) :15762-15766
[3]   Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines [J].
Bisht, Ranjana ;
Chattopadhyay, Buddhadeb .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :84-87
[4]   Computationally designed ligands enable tunable borylation of remote C-H bonds in arenes [J].
Chang, Wenju ;
Chen, Yu ;
Lu, Shuo ;
Jiao, Hongyun ;
Wang, Yajun ;
Zheng, Tianyu ;
Shi, Zhuangzhi ;
Han, Yingbin ;
Lu, Yi ;
Wang, Yi ;
Pan, Yi ;
Yu, Jin-Quan ;
Houk, Kendall N. ;
Liu, Fang ;
Liang, Yong .
CHEM, 2022, 8 (06) :1775-1788
[5]   Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction [J].
Chaturvedi, Jagriti ;
Haldar, Chabush ;
Bisht, Ranjana ;
Pandey, Gajanan ;
Chattopadhyay, Buddhadeb .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (20) :7604-7611
[6]   meta-Selective C-H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand [J].
Davis, Holly J. ;
Genov, Georgi R. ;
Phipps, Robert J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) :13351-13355
[7]   Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts [J].
Davis, Holly J. ;
Mihai, Madalina T. ;
Phipps, Robert J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) :12759-12762
[8]   Arene diversification through distal C(sp2)-H functionalization [J].
Dutta, Uttam ;
Maiti, Sudip ;
Bhattacharya, Trisha ;
Maiti, Debabrata .
SCIENCE, 2021, 372 (6543) :701-+
[9]   Copper-Catalyzed Asymmetric Defluoroborylation of 1-(Trifluoromethyl)Alkenes [J].
Gao, Pan ;
Yuan, Chengkai ;
Zhao, Yue ;
Shi, Zhuangzhi .
CHEM, 2018, 4 (09) :2201-2211
[10]   Enantioselective remote C-H activation directed by a chiral cation [J].
Genov, Georgi R. ;
Douthwaite, James L. ;
Lahdenpera, Antti S. K. ;
Gibson, David C. ;
Phipps, Robert J. .
SCIENCE, 2020, 367 (6483) :1246-+