Alkylation of furancarboxylic acid derivatives with alkenes catalyzed by nickel complexes with N-heterocyclic carbenes

被引:2
作者
Shepelenko, K. E. [1 ]
Soliev, S. B. [1 ]
Nikolaeva, K. A. [1 ]
Minyaev, M. E. [2 ]
Chernyshev, V. M. [1 ]
机构
[1] MI Platov South Russian State Polytech Univ NPI, 132 Ul Prosveshcheniya, Novocherkassk 346428, Russia
[2] Russian Acad Sci, N D Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
关键词
nickel; furans; N-heterocyclic carbenes; CH-alkylation; catalysis; DIRECT ARYLATION; 2,5-FURANDICARBOXYLIC ACID; RECENT PROGRESS; FURANS; FUNCTIONALIZATION; CONVERSION; POLYMERS;
D O I
10.1007/s11172-023-3956-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient catalytic system based on commercially available nickel source (NiCp2), N-heterocyclic carbene, and a reducing agent (HCOONa) for selective C(5)H-alkylation of amides and esters of 2-furancarboxylic acid with alkenes of various structures was developed. A series of new previously undescribed 5-alkyl derivatives of 2-furancarboxylic acid were synthesized.
引用
收藏
页码:1746 / 1752
页数:7
相关论文
共 47 条
[1]   Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877
[2]   Nickel: The "Spirited Horse" of Transition Metal Catalysis [J].
Ananikov, Valentine P. .
ACS CATALYSIS, 2015, 5 (03) :1964-1971
[3]  
[Anonymous], 2019, Bruker
[4]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[5]   Benzenesulfonyl Chlorides: Alternative Coupling Partners for Regiocontrolled Palladium-Catalyzed Direct Desulfitative 5-Arylation of Furans [J].
Beladhria, Anissa ;
Yuan, Kedong ;
Ben Ammar, Hamed ;
Soule, Jean-Francois ;
Ben Salem, Ridha ;
Doucet, Henri .
SYNTHESIS-STUTTGART, 2014, 46 (18) :2515-2523
[6]   Regioselectivity in palladium-catalysed direct arylation of 5-membered ring heteroaromatics [J].
Bheeter, Charles Beromeo ;
Chen, Lu ;
Soule, Jean-Francois ;
Doucet, Henri .
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (07) :2005-2049
[7]   Furan platform chemicals beyond fuels and plastics [J].
Bielski, Roman ;
Grynkiewicz, Grzegorz .
GREEN CHEMISTRY, 2021, 23 (19) :7458-7487
[8]   Sterically Controlled C-H Olefination of Heteroarenes [J].
Chen, Hao ;
Farizyan, Mirxan ;
Ghiringhelli, Francesca ;
van Gemmeren, Manuel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) :12213-12220
[9]   Nickel and Palladium Catalysis: Stronger Demand than Ever [J].
Chernyshev, Victor M. ;
Ananikov, Valentine P. .
ACS CATALYSIS, 2022, 12 (02) :1180-1200
[10]   Conversion of plant biomass to furan derivatives and sustainable access to the new generation of polymers, functional materials and fuels [J].
Chernyshev, Victor M. ;
Kravchenko, Oleg A. ;
Ananikov, Valentine P. .
RUSSIAN CHEMICAL REVIEWS, 2017, 86 (05) :357-387