Radical C-H arylations of (hetero)arenes catalysed by gallic acid

被引：48
作者：
Perretti, Marcelle D. [1 ]
Monzon, Diego M. [1 ]
Crisostomo, Fernando P. [1 ]
Martin, Victor S. [1 ]
Carrillo, Romen [1 ]
机构：
[1] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez IUBO, Dept Quim Organ, Ctr Invest Biomed Canarias CIBICAN, Avda Astrofis Fco Sanchez 2,Apdo Correos 456, San Cristobal la Laguna 38200, Sc De Tenerife, Spain
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 58期
关键词：
ARYL DIAZONIUM SALTS; ARENEDIAZONIUM SALTS; COUPLING REACTION; BOND FORMATION; METAL-FREE; ELECTRON; HETEROARENES; ANTIOXIDANT; DEDIAZONIATION; ACTIVATION;
D O I：
10.1039/c5cc09911k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Gallic acid efficiently catalyses radical arylations in water-acetone at room temperature. This methodology proved to be versatile and scalable. Therefore, it constitutes a greener alternative to arylation. Moreover, considering that gallic acid is an abundant vegetable tannin, this work also unleashes an alternative method for the reutilisation of bio-wastes.
引用
收藏
页码：9036 / 9039
页数：4
相关论文
共 39 条
[1]   Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation [J].
Alfonsi, Kim ;
Colberg, Juan ;
Dunn, Peter J. ;
Fevig, Thomas ;
Jennings, Sandra ;
Johnson, Timothy A. ;
Kleine, H. Peter ;
Knight, Craig ;
Nagy, Mark A. ;
Perry, David A. ;
Stefaniak, Mark .
GREEN CHEMISTRY, 2008, 10 (01) :31-36
[2]   Polyaniline-Induced CH Arylation of Arenes with Arenediazonium Salts [J].
Amaya, Toru ;
Hata, Dai ;
Moriuchi, Toshiyuki ;
Hirao, Toshikazu .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (46) :16427-16433
[3]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[4]   Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications [J].
Badhani, Bharti ;
Sharma, Neha ;
Kakkar, Rita .
RSC ADVANCES, 2015, 5 (35) :27540-27557
[5]   Mechanistic Insights into Two-Phase Radical C-H Arylations [J].
Baxter, Ryan D. ;
Liang, Yong ;
Hong, Xin ;
Brown, Timothy A. ;
Zare, Richard N. ;
Houk, K. N. ;
Baran, Phil S. ;
Blackmond, Donna G. .
ACS CENTRAL SCIENCE, 2015, 1 (08) :456-462
[6]   Organic Electron Donors as Powerful Single-Electron Reducing Agents in Organic Synthesis [J].
Broggi, Julie ;
Terme, Thierry ;
Vanelle, Patrice .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :384-413
[7]   ELUCIDATION OF ROLE OF SYN-ARYLAZO AND ANTI-ARYLAZO ALKYL ETHERS IN DEDIAZONIATION OF ARYLDIAZONIUM SALTS IN BASIC ALCOHOLIC SOLVENTS [J].
BROXTON, TJ ;
ROPER, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2157-2162
[8]   Selected patented cross-coupling reaction technologies [J].
Corbet, Jean-Pierre ;
Mignani, Gerard .
CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710
[9]   Grape Pomace as a Sustainable Source of Bioactive Compounds: Extraction, Characterization, and Biotechnological Applications of Phenolics [J].
Fontana, Ariel R. ;
Antoniolli, Andrea ;
Bottini, Ruben .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2013, 61 (38) :8987-9003
[10]   Characterization of Polyphenols and Antioxidant Potential of White Grape Pomace Byproducts (Vitis vinifera L.) [J].
Gonzalez-Centeno, Maria Reyes ;
Jourdes, Michael ;
Femenia, Antoni ;
Simal, Susana ;
Rossello, Carmen ;
Teissedre, Pierre-Louis .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2013, 61 (47) :11579-11587
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