Synthetic approach to flavanones and flavones via ligand-free palladium(II)-catalyzed conjugate addition of arylboronic acids to chromones

被引:50
作者
Kim, Donghee [1 ]
Ham, Kyungrok [1 ]
Hong, Sungwoo [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea
基金
新加坡国家研究基金会;
关键词
ASYMMETRIC 1,4-ADDITION; ALPHA; BETA-UNSATURATED KETONES; ACETYLENES; ANNULATION; ALDEHYDES; CHALCONE; CATALYST; IODIDES;
D O I
10.1039/c2ob26061a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The remarkable catalytic effects of Fe(OTf)(3) in the context of the Pd(II)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.
引用
收藏
页码:7305 / 7312
页数:8
相关论文
共 49 条
[1]   Acylated flavone C-glycosides from Cucumis sativus [J].
Abou-Zaid, MM ;
Lombardo, DA ;
Kite, GC ;
Grayer, RJ ;
Veitch, NC .
PHYTOCHEMISTRY, 2001, 58 (01) :167-172
[2]   Access to Flavones via a Microwave-Assisted, One-Pot Sonogashira-Carbonylation-Annulation Reaction [J].
Awuah, Emelia ;
Capretta, Alfredo .
ORGANIC LETTERS, 2009, 11 (15) :3210-3213
[3]   Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones [J].
Baker, W .
JOURNAL OF THE CHEMICAL SOCIETY, 1933, :1381-1389
[4]   A C2-Symmetric Chiral Bis-Sulfoxide Ligand in a Rhodium-Catalyzed Reaction: Asymmetric 1,4-Addition of Sodium Tetraarylborates to Chromenones [J].
Chen, Jun ;
Chen, Junmin ;
Lang, Feng ;
Zhang, Xiangyang ;
Cun, Linfeng ;
Zhu, Jin ;
Deng, Jingen ;
Liao, Jian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (13) :4552-+
[5]   A NEW CATALYTIC ACTIVITY OF ANTIMONY(III) CHLORIDE IN PALLADIUM(0)-CATALYZED CONJUGATE ADDITION OF AROMATICS TO ALPHA,BETA-UNSATURATED KETONES AND ALDEHYDES WITH SODIUM TETRAPHENYLBORATE AND ARYLBORONIC ACIDS [J].
CHO, CS ;
MOTOFUSA, S ;
OHE, K ;
UEMURA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :883-888
[6]   Synthesis of flavanones using nanocrystalline MgO [J].
Choudary, BM ;
Ranganath, KVS ;
Yadav, J ;
Kantam, ML .
TETRAHEDRON LETTERS, 2005, 46 (08) :1369-1371
[7]   PREPARATIVE AND REGIOCHEMICAL ASPECTS OF THE PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF 2-HYDROXYARYL IODIDES WITH ETHYNYLARENES [J].
CIATTINI, PG ;
MORERA, E ;
ORTAR, G ;
ROSSI, SS .
TETRAHEDRON, 1991, 47 (32) :6449-6456
[8]  
Craig WJ, 1999, AM J CLIN NUTR, V70, p491S, DOI 10.1093/ajcn/70.3.491s
[9]   Structure-activity relationships and molecular modeling analysis of flavonoids binding to the benzodiazepine site of the rat brain GABAA receptor complex [J].
Dekermendjian, K ;
Kahnberg, P ;
Witt, MR ;
Sterner, O ;
Nielsen, M ;
Liljefors, T .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4343-4350
[10]   Synthetic applications of rhodium catalysed conjugate addition [J].
Edwards, Hannah J. ;
Hargrave, Jonathan D. ;
Penrose, Stephen D. ;
Frost, Christopher G. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2093-2105