Palladium catalyzed regioselective distal C (sp2)-H functionalization

被引:1
作者
Chauhan, Rachit Singh [1 ]
Bairagi, Yogesh [1 ]
Desai, Om [1 ]
Kowalczyk, Rafal [2 ]
Maiti, Debabrata [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Mumbai, India
[2] Wroclaw Univ Sci & Technol, Wroclaw, Poland
关键词
H BOND FUNCTIONALIZATION; DIRECTING GROUP; OLEFINATION; ACTIVATION; TEMPLATE; ARENES; ACID; ACETOXYLATION;
D O I
10.1039/d4cc06546h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The selective functionalization of C-H bonds in arenes remains a challenging task in organic synthesis. While directing group (DG)-assisted strategies for proximal C-H activation are well-established, distal meta and para-C-H functionalization has proven more elusive and has attracted significant interest. Palladium-catalyzed C-H activation, in particular, has emerged as a promising approach for achieving site-selectivity in these transformations. This review provides a comprehensive overview of recent advances in palladium-catalyzed distal C-H functionalization, delving into mechanistic details and the scope of these strategies. By summarizing the successes and challenges in this field, we aim to illuminate potential avenues for future research and development in synthetic methodology.
引用
收藏
页码:4293 / 4315
页数:23
相关论文
共 76 条
[1]  
Achar T. K., 2019, Angew. Chem., Int. Ed., V131
[2]  
Bag S., 2017, Angew.Chem, V129, P3230, DOI DOI 10.1002/ANGE.201611360
[3]   Palladium-Catalyzed meta-C-H Allylation of Arenes: A Unique Combination of a Pyrimidine-Based Template and Hexafluoroisopropanol [J].
Bag, Sukdev ;
Surya, K. ;
Mondal, Arup ;
Jayarajan, Ramasamy ;
Dutta, Uttam ;
Porey, Sandip ;
Sunoj, Raghavan B. ;
Maiti, Debabrata .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (28) :12453-12466
[4]   Palladium-Catalyzed Selective meta-C-H Deuteration of Arenes: Reaction Design and Applications [J].
Bag, Sukdev ;
Petzold, Martin ;
Sur, Aishanee ;
Bhowmick, Suman ;
Werz, Daniel B. ;
Maiti, Debabrata .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (40) :9433-9437
[5]   Remote meta-C-H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary [J].
Bag, Sukdev ;
Jayarajan, Ramasamy ;
Dutta, Uttam ;
Chowdhury, Rajdip ;
Mondal, Rahul ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) :12538-12542
[6]   Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly [J].
Bag, Sukdev ;
Patra, Tuhin ;
Modak, Atanu ;
Deb, Arghya ;
Maity, Soham ;
Dutta, Uttam ;
Dey, Aniruddha ;
Kancherla, Rajesh ;
Maji, Arun ;
Hazra, Avijit ;
Bera, Milan ;
Maiti, Debabrata .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) :11888-11891
[7]   Meta-Selective C-H Functionalization of Arylsilanes Using a Silicon Tethered Directing Group [J].
Bang, Jaehan ;
Gi, Seyun ;
Lee, Yoonjung ;
Tan, Kian L. ;
Lee, Sunggi .
ORGANIC LETTERS, 2022, 24 (28) :5181-5185
[8]   Room-Temperature meta-Functionalization: Pd(II)-Catalyzed Synthesis of 1,3,5-Trialkenyl Arene and meta-Hydroxylated Olefin [J].
Bera, Milan ;
Sahoo, Santosh K. ;
Maiti, Debabrata .
ACS CATALYSIS, 2016, 6 (06) :3575-3579
[9]   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
[10]   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