The sustainable copper-catalyzed direct formation of highly functionalized p-quinols in water

被引:5
作者
Koszelewski, Dominik [1 ]
Paprocki, Daniel [1 ]
Brodzka, Anna [1 ]
Keciek, Aleksandra [1 ]
Wilk, Monika [1 ]
Ostaszewski, Ryszard [1 ]
机构
[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland
关键词
Carbon-carbon bond formation; Copper catalyst; Water; p-Quinols; Chemoselectivity; ORGANOLITHIUM REAGENTS; GRIGNARD-REAGENTS; CYCLOHEXADIENONES; BENZOQUINONES; OXIDATION; ALDEHYDES; ANALOGS; KETONES; ACID;
D O I
10.1016/j.scp.2021.100576
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The straightforward copper-catalyzed formation of p-quinols in water under air has been accomplished employing arylboronic acids. Various substituted p-benzoquinol derivatives of biological importance were obtained in good yield. Furthermore, the synthesis of target p-quinols under physiological conditions in serum and carbonate buffer is demonstrated. The essential features of this method are the high functional group tolerance and scalable one-pot preparation of p-quinols from corresponding arylboronic acid. Very mild reaction conditions, an absence of the heavy toxic metals, simple procedure as well as high chemoselectivity makes the established protocol desirable for academia and pharmaceutical industry laboratories.
引用
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页数:6
相关论文
共 40 条
[1]   Recent Advances in 1,4-Benzoquinone Chemistry [J].
Abraham, Ignatious ;
Joshi, Rahul ;
Pardasani, Pushpa ;
Pardasani, R. T. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2011, 22 (03) :385-421
[2]   Manumycin A: Synthesis of the (+)-enantiomer and revision of stereochemical assignment [J].
Alcaraz, L ;
Macdonald, G ;
Ragot, JP ;
Lewis, N ;
Taylor, RJK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) :3526-3527
[3]   Quinols as novel therapeutic agents. 2. 4-(1-arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2,5-dien-1-ones and related agents as potent and selective antitumor agents [J].
Berry, JM ;
Bradshaw, TD ;
Fichtner, I ;
Ren, RB ;
Schwalbe, CH ;
Wells, G ;
Chew, EH ;
Stevens, MFG ;
Westwell, AD .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (02) :639-644
[4]   Elucidation of thioredoxin as a molecular target for antitumor quinols [J].
Bradshaw, TD ;
Matthews, CS ;
Cookson, J ;
Chew, EH ;
Shah, M ;
Bailey, K ;
Monks, A ;
Harris, E ;
Westwell, AD ;
Wells, G ;
Laughton, CA ;
Stevens, MFG .
CANCER RESEARCH, 2005, 65 (09) :3911-3919
[5]   Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines [J].
Chung, Sohyun ;
Kim, Jinho .
TETRAHEDRON LETTERS, 2019, 60 (11) :792-795
[6]  
Dipakranjan M., 2008, EUR J ORG CHEM
[7]   Rh-Catalyzed arylation of fluorinated ketones with arylboronic acids [J].
Dobson, Luca S. ;
Pattison, Graham .
CHEMICAL COMMUNICATIONS, 2016, 52 (74) :11116-11119
[8]   NEW SELECTIVE CARBONYL BLOCKING GROUP - REGIOSELECTIVE PROTECTION OF PARA-QUINONES [J].
EVANS, DA ;
HOFFMAN, JM ;
TRUESDAL.LK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) :5822-5823
[9]   Antioxidant-Inspired Drug Discovery: Antitumor Metabolite Is Formed in Situ from a Hydroxycinnamic Acid Derivative upon Free-Radical Scavenging [J].
Fasi, Laura ;
Di Meo, Florent ;
Kuo, Ching-Ying ;
Buric, Sonja Stojkovic ;
Martins, Ana ;
Kusz, Norbert ;
Beni, Zoltan ;
Dekany, Miklos ;
Balogh, Gyorgy Tibor ;
Pesic, Milica ;
Wang, Hui-Chun ;
Trouillas, Patrick ;
Hunyadi, Attila .
JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (03) :1657-1668
[10]   Oxidation of 4-arylphenol trimethylsilyl ethers to p-arylquinols using hypervalent iodine(III) reagents [J].
Felpin, Francois-Xavier .
TETRAHEDRON LETTERS, 2007, 48 (03) :409-412