Iridium-catalyzed meta-selective C-H borylation of phenol derivatives

被引:1
作者
Ju, Wenjie [1 ]
Gao, Du [1 ]
Liang, Min [1 ]
Han, Shuxiong [1 ]
Liu, Chuangchuang [1 ]
Zhao, Yingsheng [1 ,2 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453000, Peoples R China
基金
中国国家自然科学基金;
关键词
AROMATIC-ALDEHYDES; DIRECTING GROUP; ACTIVATION; ARENES; COMPLEXES; LIGAND;
D O I
10.1039/d4qo00516c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective C-H functionalization of aromatics remains a challenging problem in organic synthesis, particularly for meta-selective C-H borylations of phenols derivatives. Here, pivalic acid promoted iridium-catalyzed meta-selective C-H borylation of phenols is disclosed. Various substituted phenol directives including bioactive compounds are found to be tolerated, affording the corresponding borylated products in moderate to good yields under concise reaction conditions. Regioselective C-H functionalization of aromatics remains a challenge in synthesis, particularly for meta-selective C-H borylations of phenols. Here, pivalic acid promoted iridium-catalyzed meta-selective C-H borylation of phenols is disclosed.
引用
收藏
页码:3409 / 3414
页数:6
相关论文
共 46 条
[1]   Metal-catalysed C-H bond activation and borylation [J].
Bisht, Ranjana ;
Haldar, Chabush ;
Hassan, Mirja Md Mahamudul ;
Hoque, Md Emdadul ;
Chaturvedi, Jagriti ;
Chattopadhyay, Buddhadeb .
CHEMICAL SOCIETY REVIEWS, 2022, 51 (12) :5042-5100
[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]   ortho- and meta-Selective C-H Activation and Borylation of Aromatic Aldehydes via in situ Generated Imines [J].
Bisht, Ranjana ;
Chattopadhyay, Buddhadeb .
SYNLETT, 2016, 27 (14) :2043-2050
[4]   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
[5]   Silyl-directed, iridium-catalyzed ortho-borylation of arenes. A one-pot ortho-borylation of phenols, arylamines, and alkylarenes [J].
Boebel, Timothy A. ;
Hartwig, John. F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) :7534-+
[6]   Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes [J].
Boller, TM ;
Murphy, JM ;
Hapke, M ;
Ishiyama, T ;
Miyaura, N ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14263-14278
[7]   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
[8]   Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].
Cho, JY ;
Tse, MK ;
Holmes, D ;
Maleczka, RE ;
Smith, MR .
SCIENCE, 2002, 295 (5553) :305-308
[9]   Phosphine-Directed C-H Borylation Reactions: Facile and Selective Access to Ambiphilic Phosphine Boronate Esters [J].
Crawford, Kristina M. ;
Ramseyer, Timothy R. ;
Daley, Christopher J. A. ;
Clark, Timothy B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (29) :7589-7593
[10]   Transition-metal-free B-B and B-interelement reactions with organic molecules [J].
Cuenca, Ana B. ;
Shishido, Ryosuke ;
Ito, Hajime ;
Fernandez, Elena .
CHEMICAL SOCIETY REVIEWS, 2017, 46 (02) :415-430