65171-00-8Relevant academic research and scientific papers
Nickel-catalyzed asymmetric Ullmann Coupling for the synthesis of axially chiral tetra-ortho-substituted biaryl dials
Chen, Wen-Wen,Zhao, Qian,Xu, Ming-Hua,Lin, Guo-Qiang
, p. 1072 - 1075 (2010)
(Figure Presented) The first example of nickel-catalyzed asymmetric Ullmann coupling of bls-ortho-substltuted arylhalldes is described. With the chlral BINOLbased monodentate phosphoramldite ligand, the reaction allows atropoenantloselectlve synthesis of a series of axially chiral tetra-orthosubstltuted biaryl dials. By taking advantage on this asymmetric Ullman coupling as a key stereogenlc axis-forming reaction, the formal synthesis of (+)-isoschizandrin was accomplished.
Tubulin-binding dibenz[c,e]oxepines as colchinol analogues for targeting tumour vasculature
Edwards, David J.,Hadfield, John A.,Wallace, Timothy W.,Ducki, Sylvie
supporting information; experimental part, p. 219 - 231 (2011/02/23)
Various methoxy- and hydroxy-substituted dibenz[c,e]oxepines were prepared via the copper(i)-induced coupling of ether-tethered arylstannanes or the dehydrative cyclisation of 1,1′-biphenyl-2,2′-dimethanols, assembled using the Ullmann cross-coupling of ortho-bromoaryl carbonyl compounds. The dibenzoxepines were screened for their ability to inhibit tubulin polymerisation and the in vitro growth of K562 human chronic myelogenous leukemia cells. The most active was 5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol, whose tubulin inhibitory and cytotoxicity (IC50) values were 1 μM and 40 nM, respectively.
CHEMICAL COMPOUNDS
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Page/Page column 68, (2008/12/06)
A compound of formula (I) is described; wherein the substituents are as defined in the text and wherein the compound is intended for use in the production of a vascular damaging effect in a warm-blooded animal.
A novel nickel(0)-catalyzed cascade Ullmann-pinacol coupling: From o-bromobenzaldehyde to trans-9,10-dihydroxy-9,10-dihydrophenanthrene
Lin, Shuang-Zheng,Chen, Qing-An,You, Tian-Pa
, p. 2101 - 2105 (2008/02/09)
Using 5 mol% of (Ph3P)2NiCl2 as a catalyst, Zn powder as a reductant, ortho-carbonyl-substituted aryl halides could be coupled to form trans-9,10-dihydroxy-9,10-dihydrophenanthrenes in a one-pot cascade reaction. Georg Thieme Verlag Stuttgart.
SYNTHESES TOTALES ET ETUDES DE LIGNANES BIOLOGIQUEMENT ACTIFS-I. APPLICATION DE LA REACTION D'ULLMANN A LA SYNTHESE DE BIARYLES PRECURSEURS DE LIGNANES BISBENZOCYCLOOCTADIENES
Brown, Eric,Robin, Jean-Pierre,Dhal, Robert
, p. 2569 - 2580 (2007/10/02)
Several biaryls bearing various substituents on both rings were synthesized in a preparativ fashion, and in yields up to 88percent by a technical improvement on the classical Ullmann reaction.All these biaryls bear reactive functional groups (i.e. formyl, methoxycarbonyl, dimethoxycarbonylpropyl and butanolidylmethyl) in both the o and o' positions.The biaryls 9, 13, 21 and 26-33 are plausible synthons for bisbenzocyclooctadiene lignans such as schizandrin and steganacin.
