Rhodium-Catalyzed Direct Allylation of Simple Arenes by Using Gem -Difluorinated Cyclopropanes as Allyl Surrogates

被引:14
作者
Jiang, Zhong-Tao
Zeng, Yaxin
Xia, Ying [1 ]
机构
[1] Sichuan Univ, West China Sch Publ Hlth, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
difluorocyclopropanes; transition-metal catalysis; allylation; C-C bond activation; rhodium catalysis; arenes; C-H ALLYLATION; ACTIVATION; ALKYLATION; ARYL; DERIVATIVES; INDOLES; ACCESS; BONDS;
D O I
10.1055/a-1536-2738
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Gem -difluorinated cyclopropanes have become an important type of allyl surrogate in transition-metal-catalyzed ring-opening processes, as demonstrated recently through various important advances, especially with palladium catalysis. The versatile fluorinated allyl species generated in this way from gem -difluorinated cyclopropanes exhibit unique advantages compared with conventional allyl sources. By using gem -difluorinated cyclopropanes as allyl surrogates, we achieved a direct allylation of simple arenes through rhodium catalysis under mild conditions. This transformation permits directing-group-free allylation of simple arenes, including electron-neutral, electron-rich, and electron-deficient ones. Here, we give a brief introduction to this area and we discuss our thoughts regarding our recent work and its design. 1 Introduction 2 Our Design 3 Condition Optimization and Substrate Scope 4 Applications in Synthesis 5 Mechanistic Discussions 6 Conclusion and Outlook
引用
收藏
页码:1675 / 1682
页数:8
相关论文
共 69 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]   Access to Divergent Fluorinated Enynes and Arenes via Palladium-Catalyzed Ring-Opening Alkynylation of gem-Difluorinated Cyclopropanes [J].
Ahmed, Ebrahim-Alkhalil M. A. ;
Suliman, Ayman M. Y. ;
Gong, Tian-Jun ;
Fu, Yao .
ORGANIC LETTERS, 2020, 22 (04) :1414-1419
[3]   Palladium-Catalyzed Stereoselective Defluorination Arylation/Alkenylation/Alkylation of gem-Difluorinated Cyclopropanes [J].
Ahmed, Ebrahim-Alkhalil M. A. ;
Suliman, Ayman M. Y. ;
Gong, Tian-Jun ;
Fu, Yao .
ORGANIC LETTERS, 2019, 21 (14) :5645-5649
[4]   Iron-Catalyzed Ortho-Allylation of Aromatic Carboxamides with Allyl Ethers [J].
Asako, Sobi ;
Ilies, Laurean ;
Nakamura, Eiichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (47) :17755-17757
[5]   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
[6]   Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation [J].
Banik, Steven M. ;
Mennie, Katrina M. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (27) :9152-9155
[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]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895
[9]   Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].
Bouchy, A ;
Rinaldi, D ;
Rivail, JL .
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281
[10]   Regioselective Intermolecular Allylic C-H Amination of Disubstituted Olefins via Rhodium/π-Allyl Intermediates [J].
Burman, Jacob S. ;
Blakey, Simon B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (44) :13666-13669