A Versatile Approach for the Synthesis of para-Substituted Arenes via Palladium-Catalyzed C-H Functionalization and Protodecarboxylation of Benzoic Acids

被引:17
作者
Pan, Shulei
Zhou, Bo
Zhang, Yanghui [1 ]
Shao, Changdong
Shi, Guangfa
机构
[1] Tongji Univ, Dept Chem, Shanghai Key Lab Chem Assessment & Sustainabil, Shanghai 200092, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H activation; palladium; decarboxylation; arenes; regioselectivity; DIRECT ORTHO-ARYLATION; SELECTIVE ARYLATION; COUPLING REACTIONS; DIRECTING GROUP; ARYL ETHERS; META; OLEFINATION; ACTIVATION; BONDS; BORYLATION;
D O I
10.1055/s-0035-1560579
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
While a great number of ortho C-H functionalization reactions have been developed and several breakthroughs have been achieved in meta C-H activation, para C-H functionalization is still in its infancy stage. In this article, a versatile strategy for the synthesis of para-substituted arenes has been developed via a tandem process consisting of palladium-catalyzed C-H functionalization and subsequent copper-catalyzed protodecarboxylation of benzoic acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the para positions of arenes bearing a variety of substituents.
引用
收藏
页码:277 / 281
页数:5
相关论文
共 90 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]  
[Anonymous], ANGEW CHEM
[3]  
[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666
[4]  
[Anonymous], 2011, ANGEW CHEM
[5]  
[Anonymous], ANGEW CHEM
[6]  
[Anonymous], 2013, Angew. Chem, DOI DOI 10.1002/ANGE.201301451
[7]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[8]   Direct ortho-Arylation of ortho-Substituted Benzoic Acids: Overriding Pd-Catalyzed Protodecarboxylation [J].
Arroniz, Carlos ;
Ironmonger, Alan ;
Rassias, Gerry ;
Larrosa, Igor .
ORGANIC LETTERS, 2013, 15 (04) :910-913
[9]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[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