Pd-Catalyzed Remote Meta-C-H Functionalization of Phenylacetic Acids Using a Pyridine Template

被引:59
作者
Jin, Zhong [1 ]
Chu, Ling [1 ]
Chen, Yan-Qiao [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
基金
美国国家科学基金会;
关键词
U-SHAPED TEMPLATE; DIRECTING GROUP; OLEFINATION; ARYLATION; LIGAND; ARENES; ACTIVATION; ALKYLATION; BORYLATION; BONDS;
D O I
10.1021/acs.orglett.7b03336
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective pyridine based U-shaped template has been developed to enable a diverse range of meta-C-H functionalizations of phenylacetic acid scaffolds. This, new template has extended the reaction scope to cross-coupling with ArBF3K as well as iodination using 1,3-cliiodo-5,5-dinriethylhydantoin as the iodination reagent.
引用
收藏
页码:425 / 428
页数:4
相关论文
共 34 条
[1]   Template-Assisted meta-C-H Alkylation and Alkenylation of Arenes [J].
Bag, Sukdev ;
Jayarajan, Ramasamy ;
Mondal, Rahul ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) :3182-3186
[2]   Palladium(II)-Catalyzed meta-C-H Olefination: Constructing Multisubstituted Arenes through Homo-Diolefination and Sequential Hetero-Diolefination [J].
Bera, Milan ;
Maji, Arun ;
Sahoo, Santosh K. ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (29) :8515-8519
[3]   Meta-Selective Arene C-H Bond Olefination of Arylacetic Acid Using a Nitrile-Based Directing Group [J].
Bera, Milan ;
Modak, Atanu ;
Patra, Tuhin ;
Maji, Arun ;
Maiti, Debabrata .
ORGANIC LETTERS, 2014, 16 (21) :5760-5763
[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]   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
[6]   Remote Meta-C-H Activation Using a Pyridine-Based Template: Achieving Site-Selectivity via the Recognition of Distance and Geometry [J].
Chu, Ling ;
Shang, Ming ;
Tanaka, Keita ;
Chen, Qinghao ;
Pissarnitski, Natalya ;
Streckfuss, Eric ;
Yu, Jin-Quan .
ACS CENTRAL SCIENCE, 2015, 1 (07) :394-399
[7]   Pd(II)-Catalyzed ortho- or meta-C-H Olefination of Phenol Derivatives [J].
Dai, Hui-Xiong ;
Li, Gang ;
Zhang, Xing-Guo ;
Stepan, Antonia F. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7567-7571
[8]   Remote meta-C-H Olefination of Phenylacetic Acids Directed by a Versatile U-Shaped Template [J].
Deng, Youqian ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) :888-891
[9]   Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis [J].
Dong, Zhe ;
Wang, Jianchun ;
Dong, Guangbin .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) :5887-5890
[10]   Copper(II)-Catalyzed meta-Selective Direct Arylation of α-Aryl Carbonyl Compounds [J].
Duong, Hung A. ;
Gilligan, Ruth E. ;
Cooke, Michael L. ;
Phipps, Robert J. ;
Gaunt, Matthew J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :463-466