Recent Advances in Copper-Catalyzed Functionalization of Unactivated C(sp3)-H Bonds

被引:9
作者
Deshpande, Neha [1 ]
Satani, Piyushkumar [1 ]
Bharodiya, Akshay [1 ]
Naveen, Togati [1 ]
机构
[1] Sardar Vallabhbhai Natl Inst Technol, Dept Chem, Surat 395007, Gujarat, India
关键词
C(sp(3))-H functionalization; Copper catalysis; C-H ALKYLATION; CROSS-COUPLING REACTIONS; INTRAMOLECULAR SILYLATION; BENZYLIC BORYLATION; PALLADIUM; ACTIVATION; AMINATION; ARYLATION; AMIDATION; ETHERS;
D O I
10.1002/ajoc.202200532
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C(sp(3))-H functionalization is a core part of organic chemistry because of the presence of C(sp(3))-H bonds in various organic molecules. However, since most C(sp(3))-H bonds are non-reactive, their functionalization is an uphill task. Standard methods of functionalization employ pre-functionalized reactants, expensive organometallic reagents, strong acids or bases and similar other harsh reaction conditions. These methods eventually affect the reaction and prevent it from yielding optimum results. Transition metal-based catalysts like Pd, Rh and Ru provide a direct functionalization route without unwanted pre-functionalization steps. These catalysts furnish superior results under mild reaction conditions. But, their expense, toxicity and low natural abundance prevent them from achieving ideality. Therefore, 3d transition metal catalysts like Mn, Fe, Co, Ni and Cu catalysts have gained significance as an alternative for conventional transition metal catalysts due to their high natural abundance, low toxicity and affordability. Copper-based catalysts are particularly important owing to the wide range of oxidation states of copper and the facile tunability of their catalytic properties. Hence, an immense amount of research is being conducted on the catalytic activity of copper for C(sp(3))-H functionalization. This review aims to provide a detailed overview of some recent reports on C(sp(3))-H functionalization using catalytic systems based on copper.
引用
收藏
页数:20
相关论文
共 279 条
[1]   C-H Functionalization of BN-Aromatics Promoted by Addition of Organolithium Compounds to the Boron Atom [J].
Abengozar, Alberto ;
Angel Fernandez-Gonzalez, Miguel ;
Sucunza, David ;
Manuel Frutos, Luis ;
Salgado, Antonio ;
Garcia-Garcia, Patricia ;
Vaquero, Juan J. .
ORGANIC LETTERS, 2018, 20 (16) :4902-4906
[2]   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
[3]   Recent development in transition metal-catalysed C-H olefination [J].
Ali, Wajid ;
Prakash, Gaurav ;
Maiti, Debabrata .
CHEMICAL SCIENCE, 2021, 12 (08) :2735-2759
[4]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[5]   Iron-Catalyzed Intramolecular Aminations of C(sp3)-H Bonds in Alkylaryl Azides [J].
Alt, Isabel T. ;
Guttroff, Claudia ;
Plietker, Bernd .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (35) :10582-10586
[6]  
[Anonymous], 2021, ANGEW CHEM, V133, P5907
[7]  
[Anonymous], 2017, ANGEW CHEM, V129, P16777
[8]  
[Anonymous], 2004, ANGEW CHEM, V116, P2256
[9]  
[Anonymous], 2017, ANGEW CHEM, V129, P10718
[10]  
[Anonymous], 2018, ANGEW CHEM, V130, P4309