Toolbox for Distal C-H Bond Functionalizations in Organic Molecules

被引:369
作者
Sinha, Soumya Kumar [1 ]
Guin, Srimanta [1 ]
Maiti, Sudip [1 ]
Biswas, Jyoti Prasad [1 ]
Porey, Sandip [1 ]
Maiti, Debabrata [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India
关键词
CATALYZED INTRAMOLECULAR AMINATION; CROSS-COUPLING REACTIONS; UNACTIVATED C(SP(3))-H BONDS; ARYL-ALPHA-DIAZOACETATES; CO(II)-BASED METALLORADICAL CATALYSIS; RADICAL TRANSLOCATION REACTIONS; TRACELESS DIRECTING GROUPS; PARA-SELECTIVE ALKYLATION; DIRECT ORTHO-ARYLATION; CARBON-HYDROGEN-BONDS;
D O I
10.1021/acs.chemrev.1c00220
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition-metal-catalyzed C-H activation has developed a contemporary approach to the omnipresent area of retrosynthetic disconnection. Scientific researchers have been tempted to take the help of this methodology to plan their synthetic discourses. This paradigm shift has helped in the development of industrial units as well, making the synthesis of natural products and pharmaceutical drugs step-economical. In the vast zone of C-H bond activation, the functionalization of proximal C-H bonds has gained utmost popularity. Unlike the activation of proximal C-H bonds, the distal C-H functionalization is more strenuous and requires distinctly specialized techniques. In this review, we have compiled various methods adopted to functionalize distal C-H bonds, mechanistic insights within each of these procedures, and the scope of the methodology. With this review, we give a complete overview of the expeditious progress the distal C-H activation has made in the field of synthetic organic chemistry while also highlighting its pitfalls, thus leaving the field open for further synthetic modifications.
引用
收藏
页码:5682 / 5841
页数:160
相关论文
共 604 条
[1]   Recent applications of C-H functionalization in complex natural product synthesis [J].
Abrams, Dylan J. ;
Provencher, Philip A. ;
Sorensen, Erik J. .
CHEMICAL SOCIETY REVIEWS, 2018, 47 (23) :8925-8967
[2]   Palladium-Catalyzed Template Directed C-5 Selective Olefination of Thiazoles [J].
Achar, Tapas Kumar ;
Biswas, Jyoti Prasad ;
Porey, Sandip ;
Pal, Tapas ;
Ramakrishna, Kankanala ;
Maiti, Siddhartha ;
Maiti, Debabrata .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12) :8315-8321
[3]   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
[4]   Regiocontrolled Remote C-H Olefination of Small Heterocycles [J].
Achar, Tapas Kumar ;
Ramakrishna, Kankanala ;
Pal, Tapas ;
Porey, Sandip ;
Dolui, Pravas ;
Biswas, Jyoti Prasad ;
Maiti, Debabrata .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (68) :17906-17910
[5]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[6]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[7]   Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines [J].
Ackermann, Lutz ;
Hofmann, Nora ;
Vicente, Ruben .
ORGANIC LETTERS, 2011, 13 (07) :1875-1877
[8]   Orthogonal Selectivity in C-H Olefination: Synthesis of Branched Vinylarene with Unactivated Aliphatic Substitution [J].
Agasti, Soumitra ;
Mondal, Bhaskar ;
Achar, Tapas Kumar ;
Sinha, Soumya Kumar ;
Suseelan, Anjana Sarala ;
Szabo, Kalman J. ;
Schoenebeck, Franziska ;
Maiti, Debabrata .
ACS CATALYSIS, 2019, 9 (10) :9606-9613
[9]   Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901
[10]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311