Palladium-catalyzed C(sp3)-C(sp2) coupling: synthesis of C(3)-arylphthalides

被引:0
作者
Rao, H. Surya Prakash [1 ,2 ]
Prabhakaran, J. [1 ]
机构
[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
[2] Teadus Pharm Pvt Ltd, Hyderabad 500072, Telangana, India
关键词
Arylphthalides; Suzuki coupling; Palladium; Coupling reactions; ACTIVE METHYLENE-COMPOUNDS; 3-SUBSTITUTED ISOBENZOFURANONES; PHTHALIDES; CHEMISTRY; COROLLOSPORINE; METHODOLOGIES; INHIBITORS; ALDEHYDES;
D O I
10.1007/s11696-024-03520-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have achieved an efficient synthesis of C(3)-arylphthalides by coupling C(3)-bromophthalides and arylboronic acids under palladium catalysis. The C(sp(3))-C(sp(2)) coupling worked well in the presence of water to provide products in a high yield.
引用
收藏
页码:5985 / 5991
页数:7
相关论文
共 46 条
[1]  
Armarego W.L. F., 2003, Purification of Laboratory Chemicals, V5th
[2]   Secondary mould metabolites.: Part 60.: Cryphonectric acid and other minor metabolites from a hypovirulent strain of Cryphonectria parasitica [J].
Arnone, A ;
Assante, G ;
Nasini, G ;
Strada, S ;
Vercesi, A .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (01) :48-50
[3]   Recent advancements in synthetic methodologies of 3-substituted phthalides and their application in the total synthesis of biologically active natural products [J].
Awasthi, Amardeep ;
Singh, Mandeep ;
Rathee, Garima ;
Chandra, Ramesh .
RSC ADVANCES, 2020, 10 (21) :12626-12652
[4]   The structural diversity of phthalides from the Apiaceae [J].
Beck, John J. ;
Chou, Shen-Chieh .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (05) :891-900
[5]  
CANONNE P, 1988, TETRAHEDRON, V44, P2903
[6]   Novel phthalide derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo [J].
Chen, Liu Zeng ;
Wu, Jing ;
Li, Kang ;
Wu, Qian Qian ;
Chen, Rui ;
Liu, Xin Hua ;
Ruan, Ban Feng .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 206
[7]   Mechanistic Aspects of the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction [J].
D'Alterio, Massimo C. ;
Casals-Cruanas, Eric ;
Tzouras, Nikolaos V. ;
Talarico, Giovanni ;
Nolan, Steven P. ;
Poater, Albert .
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (54) :13481-13493
[8]   Active Methylene Compounds in the Synthesis of 3-substituted Isobenzofuranones, Isoindolinones and Related Compounds [J].
Di Mola, Antonia ;
Palombi, Laura ;
Massa, Antonio .
CURRENT ORGANIC CHEMISTRY, 2012, 16 (19) :2302-2320
[9]   Active methylene compounds in a very effective approach to 3-substituted isobenzofuranones through tandem aldol/lactonization reactions [J].
Di Mola, Antonia ;
Croce, Gianluca ;
More, Vijaykumar ;
De Caprariis, Paolo ;
Filosa, Rosanna ;
Massa, Antonio .
TETRAHEDRON, 2012, 68 (31) :6146-6151
[10]   Synthesis of 1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol [J].
Hernandez, Eliud ;
Velez, Jessica M. ;
Vlaar, Cornelis P. .
TETRAHEDRON LETTERS, 2007, 48 (51) :8972-8975