Direct Decarboxylative Meta-Selective Acylation of Arenes via an Ortho-Ruthenation Strategy

被引:64
作者
Jing, Kun [1 ,2 ]
Li, Zhong-Yuan [1 ,2 ]
Wang, Guan-Wu [1 ,2 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Collaborat Innovat Ctr Chem Energy Mat iChEM,Ctr, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
关键词
meta-selectivity; decarboxylative acylation; ruthenium catalysis; ortho-metalation; alpha-oxocarboxylic acids; radical process; H BOND FUNCTIONALIZATION; ALPHA-OXOCARBOXYLIC ACIDS; AROMATIC KETONES; ALKYLATION; ACTIVATION; NITRATION; DIFLUOROMETHYLATION; REGIOSELECTIVITY; BROMINATION; SECONDARY;
D O I
10.1021/acscatal.8b03695
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The direct decarboxylative meta-selective C-H acylation of a wide range of arenes is established via the ruthenium-catalyzed ortho-metalation strategy. This procedure, using Ru-3(CO)(12) as the catalyst and a-oxocarboxylic acids as the acylation source, featured broad substrate scope, good functional group tolerance, and high regioselectivity. Mechanistic studies demonstrated that a radical process and an 18e-octahedral ruthenium species were involved in this reaction. The present work provides a new strategy for the regioselective metaacylation reactions and will be a powerful tool for the development of pharmaceutical and materials science.
引用
收藏
页码:11875 / 11881
页数:13
相关论文
共 57 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines [J].
Ackermann, Lutz ;
Hofmann, Nora ;
Vicente, Ruben .
ORGANIC LETTERS, 2011, 13 (07) :1875-1877
[2]   Ruthenium-Catalyzed C-H Bond Functionalizations of 1,2,3-Triazol-4-yl-Substituted Arenes: Dehydrogenative Couplings Versus Direct Arylations [J].
Ackermann, Lutz ;
Novak, Petr ;
Vicente, Ruben ;
Pirovano, Valentina ;
Potukuchi, Harish K. .
SYNTHESIS-STUTTGART, 2010, (13) :2245-2253
[3]   Regioselective, directed meta acylation of aromatic compounds [J].
Akai, S ;
Peat, AJ ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9119-9125
[4]   Ruthenium diacetate-catalysed oxidative alkenylation of C-H bonds in air: synthesis of alkenyl N-arylpyrazoles [J].
Arockiam, Percia B. ;
Fischmeister, Cedric ;
Bruneau, Christian ;
Dixneuf, Pierre H. .
GREEN CHEMISTRY, 2011, 13 (11) :3075-3078
[5]   Ruthenium-Catalyzed meta-Carboxylation [J].
Barlow, Helen L. ;
Teskey, Christopher J. ;
Greaney, Michael F. .
ORGANIC LETTERS, 2017, 19 (24) :6662-6665
[6]   Photosensitizing drugs containing the benzophenone chromophore [J].
Bosca, F ;
Miranda, MA .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1998, 43 (01) :1-26
[7]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[8]   Ligand-promoted ruthenium-catalyzed meta C-H chlorination of arenes using N-chloro-2,10-camphorsultam [J].
Fan, Zhoulong ;
Lu, Heng ;
Cheng, Zhen ;
Zhang, Ao .
CHEMICAL COMMUNICATIONS, 2018, 54 (47) :6008-6011
[9]   PMes3-Promoted Ruthenium-Catalyzed Meta C-H Nitration of 6-Arylpurines [J].
Fan, Zhoulong ;
Lu, Heng ;
Zhang, Ao .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (06) :3245-3251
[10]   Monomeric Octahedral Ruthenium(II) Complex Enabled meta-C-H Nitration of Arenes with Removable Auxiliaries [J].
Fan, Zhoulong ;
Li, Jie ;
Lu, Heng ;
Wang, Dong-Yu ;
Wang, Chao ;
Uchiyama, Masanobu ;
Zhang, Ao .
ORGANIC LETTERS, 2017, 19 (12) :3199-3202