Palladium-Catalyzed Distal m-C-H Functionalization of Arylacetic Acid Derivatives

被引：16

作者：

Srinivas, Dasari ^{[1
]}

Satyanarayana, Gedu ^{[1
]}

机构：

[1] Indian Inst Technol Hyderabad, Dept Chem, Sangareddy 502285, Telangana, India

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 19期

关键词：

DIRECTING GROUPS; BOND FUNCTIONALIZATION; OLEFINATION; ACTIVATION; ARYLATION; ACETOXYLATION; TEMPLATE; ARENES;

D O I：

10.1021/acs.orglett.1c02460

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we present m-C-H olefination on derivatives of phenylacetic acids by tethering with a simple nitrile-based template through palladium catalysis. Notably, the versatility of the method is evaluated with a wide range of phenylacetic acid derivatives for obtaining the meta-olefination products in fair to excellent yields with outstanding selectivities under mild conditions. Significantly, the present strategy is successfully exemplified for the synthesis of drugs/natural product analogues (naproxen, ibuprofen, paracetamol, and cholesterol).

引用

页码：7353 / 7358

页数：6

共 60 条

[1] Palladium-Catalyzed Directed meta-Selective C-H Allylation of Arenes: Unactivated Internal Olefins as Allyl Surrogates [J].

Achar, Tapas Kumar ;

Zhang, Xinglong ;

Mondal, Rahul ;

Shanavas, M. S. ;

Maiti, Siddhartha ;

Maity, Sabyasachi ;

Pal, Nityananda ;

Paton, Robert S. ;

Maiti, Debabrata .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (30) :10353-10360

[2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[3] Imine as a linchpin approach for meta-C-H functionalization [J].

Bag, Sukdev ;

Jana, Sadhan ;

Pradhan, Sukumar ;

Bhowmick, Suman ;

Goswami, Nupur ;

Sinha, Soumya Kumar ;

Maiti, Debabrata .

NATURE COMMUNICATIONS, 2021, 12 (01)

[4] 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

[5] 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

[6] 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

[7] 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

[8] 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

[9] Direct meta-C-H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine-Based Template [J].

Brochetta, Massimo ;

Borsari, Tania ;

Bag, Sukdev ;

Jana, Sadhan ;

Maiti, Siddhartha ;

Porta, Alessio ;

Werz, Daniel B. ;

Zanoni, Giuseppe ;

Maiti, Debabrata .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (44) :10323-10327

[10] 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

← 1 2 3 4 5 6 →