Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction

被引:75
作者
Chaturvedi, Jagriti [1 ,2 ]
Haldar, Chabush [1 ]
Bisht, Ranjana [1 ]
Pandey, Gajanan [2 ]
Chattopadhyay, Buddhadeb [1 ]
机构
[1] Ctr Biomed Res, Div Mol Synth & Drug Discovery, Lucknow 226014, Uttar Pradesh, India
[2] Babasaheb Bhimrao Ambedkar Univ, Dept Appl Chem, Lucknow 226025, Uttar Pradesh, India
关键词
ACTIVATION; ARENES; LIGAND; AROMATICS;
D O I
10.1021/jacs.1c01770
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.
引用
收藏
页码:7604 / 7611
页数:8
相关论文
共 55 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]   1,10-Phenanthroline: A versatile building block for the construction of ligands for various purposes [J].
Bencini, Andrea ;
Lippolis, Vito .
COORDINATION CHEMISTRY REVIEWS, 2010, 254 (17-18) :2096-2180
[3]   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
[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]   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
[6]   Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions [J].
Chattopadhyay, Buddhadeb ;
Dannatt, Jonathan E. ;
Andujar-De Sanctis, Ivonne L. ;
Gore, Kristin A. ;
Maleczka, Robert E., Jr. ;
Singleton, Daniel A. ;
Smith, Milton R., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) :7864-7871
[7]   Steric and chelate directing effects in aromatic borylation [J].
Cho, JY ;
Iverson, CN ;
Smith, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12868-12869
[8]   Cleavage of C(aryl)-CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions [J].
Dai, Peng-Fei ;
Ning, Xiao-Shan ;
Wang, Hua ;
Cui, Xian-Chao ;
Liu, Jie ;
Qu, Jian-Ping ;
Kang, Yan-Biao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (16) :5392-5395
[9]   Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Do, Hien-Quang ;
Shabashov, Dmitry .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086
[10]   Recent Advances in C-H Functionalization [J].
Davies, Huw M. L. ;
Morton, Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (02) :343-350