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Axially Chiral Bifunctional 8,8'-Biquinolyl: Synthesis of 7,7'-Dihydroxymethyl-8,8'-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7'-Dimethyl-8,8'-biquinolyl.
Kitamura M, Fukuma H, Kobayashi M, Okayama S, Okauchi T. Kitamura M, et al. J Org Chem. 2016 May 6;81(9):3956-60. doi: 10.1021/acs.joc.6b00534. Epub 2016 Apr 12. J Org Chem. 2016. PMID: 27042866
Bifunctional C2-symmetric 7,7'-dihydroxymethyl-8,8'-biquinolyl (2) was synthesized in short steps via (i) Cu/Pd-catalyzed homo coupling of 7-methyl-8-bromoquinoline and (ii) Pd(II)-catalyzed double C-H oxidation. Axial chirality of 2 and its synthetic precursor 7,7'-dimeth …
Bifunctional C2-symmetric 7,7'-dihydroxymethyl-8,8'-biquinolyl (2) was synthesized in short steps via (i) Cu/Pd-catalyzed homo coupli …
Enzymatic resolution of 7,7'-dihydroxy-8,8'- biquinolyl dipentanoate and its conversion to 2,2'-di-tert-butyl-7,7'-dihydroxy-8,8'-biquinolyl.
Blakemore PR, Milicevic SD, Zakharov LN. Blakemore PR, et al. J Org Chem. 2007 Nov 23;72(24):9368-71. doi: 10.1021/jo701611u. Epub 2007 Nov 1. J Org Chem. 2007. PMID: 17973531
Incubation of (+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl (4) with a crude cholesterol esterase preparation (from bovine pancreas) yielded highly enantioenriched unreacted dextrorotatory material, (+)-(aR)-4 (46%, > or = 99% ee), accompanied by the expected diol product …
Incubation of (+/-)-7,7'-di(pentanoyloxy)-8,8'-biquinolyl (4) with a crude cholesterol esterase preparation (from bovine pancreas) yi …
Synthesis of 7,7'-dihydroxy-8,8'-biquinolyl (azaBINOL) via Pd-catalyzed directed double C-H functionalization of 8,8'-biquinolyl: emergence of an atropos from a tropos state.
Wang C, Flanigan DM, Zakharov LN, Blakemore PR. Wang C, et al. Org Lett. 2011 Aug 5;13(15):4024-7. doi: 10.1021/ol201539d. Epub 2011 Jun 29. Org Lett. 2011. PMID: 21714530
7,7'-Dihydroxy-8,8'-biquinolyl (azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C-H functionalization of 8,8'-biquinolyl mediated by PhI(OAc)(2) …
7,7'-Dihydroxy-8,8'-biquinolyl (azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed …
Computational exploration of the mechanism of alcohol oxidation by dioxygen activated with biquinolyl-containing cu complexes.
Polestshuk PM, Magdesieva TV. Polestshuk PM, et al. Inorg Chem. 2010 Apr 5;49(7):3370-86. doi: 10.1021/ic9024537. Inorg Chem. 2010. PMID: 20184372
The mechanism of benzyl alcohol oxidation with dioxygen activated by Cu complexes with biquinolyl (biQ)-containing ligands was investigated using theoretical DFT calculations to identify the active species and to reveal similarities with naturally occurring oxidations perf …
The mechanism of benzyl alcohol oxidation with dioxygen activated by Cu complexes with biquinolyl (biQ)-containing ligands was invest …
Resolution, enantiomerization kinetics, and chiroptical properties of 7,7'-dihydroxy-8,8'-biquinolyl.
Blakemore PR, Kilner C, Milicevic SD. Blakemore PR, et al. J Org Chem. 2006 Oct 13;71(21):8212-8. doi: 10.1021/jo061608e. J Org Chem. 2006. PMID: 17025314
(+/-)-7,7'-Dihydroxy-8,8'-biquinolyl (6) was resolved into its enantiomorphic atropisomers via reverse phase (C18) chromatographic separation of epimeric bismenthyl carbonates, (-)-lk-9 and (+)-ul-9, derived from 6 and (+)-menthyl chloroformate. ...Saponification of the se …
(+/-)-7,7'-Dihydroxy-8,8'-biquinolyl (6) was resolved into its enantiomorphic atropisomers via reverse phase (C18) chromatographic se …
Effect of chromium(III) and of other ions on the absorptiometric determination of copper with 2, 2'-biquinolyl.
Irving HM, Tomlinson WR. Irving HM, et al. Talanta. 1968 Nov;15(11):1267-79. doi: 10.1016/0039-9140(68)80049-9. Talanta. 1968. PMID: 18960429
In the determination of small amounts of copper in certain alloys by liquid-liquid extraction of the bis-chelate of copper(I) with 2, 2'-biquinolyl, recovery of copper has been reported to be low when chromium(III) is present. ...
In the determination of small amounts of copper in certain alloys by liquid-liquid extraction of the bis-chelate of copper(I) with 2, 2'- …
Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C-H homocoupling of quinoline N-oxides.
Stephens DE, Lakey-Beitia J, Chavez G, Ilie C, Arman HD, Larionov OV. Stephens DE, et al. Chem Commun (Camb). 2015 Jun 11;51(46):9507-10. doi: 10.1039/c5cc02227d. Chem Commun (Camb). 2015. PMID: 25966913 Free PMC article.
A novel site-selective palladium-catalyzed oxidative C8-H homocoupling reaction of quinoline N-oxides has been developed. The reaction affords substituted 8,8'-biquinolyl N,N'-dioxides that can be readily converted to a variety of functionalized 8,8'-biquinolyls. ...
A novel site-selective palladium-catalyzed oxidative C8-H homocoupling reaction of quinoline N-oxides has been developed. The reaction affor …
Harnessing anionic rearrangements on the benzenoid ring of quinoline for the synthesis of 6,6'-disubstituted 7,7'-dihydroxy-8,8'-biquinolyls.
Blakemore PR, Kilner C, Milicevic SD. Blakemore PR, et al. J Org Chem. 2005 Jan 7;70(1):373-6. doi: 10.1021/jo048258l. J Org Chem. 2005. PMID: 15624954
7,7'-Bis(((dimethylamino)carbonyl)oxy)-8,8'-biquinolyl (5) was prepared in 71% yield by regioselective directed ortho metalation (DoM) of N,N-dimethyl O-quinol-7-yl carbamate (2) with LDA followed by oxidation with anhydrous ferric chloride. DoM of 5 with excess LDA induce …
7,7'-Bis(((dimethylamino)carbonyl)oxy)-8,8'-biquinolyl (5) was prepared in 71% yield by regioselective directed ortho metalation (DoM …
Syntheses, structures and spectroscopy of uni- and bi-dentate nitrogen base complexes of silver(I) trifluoromethanesulfonate.
Di Nicola C, Effendy, Marchetti F, Nervi C, Pettinari C, Robinson WT, Sobolev AN, White AH. Di Nicola C, et al. Dalton Trans. 2010 Jan 21;39(3):908-22. doi: 10.1039/b913173f. Epub 2009 Nov 17. Dalton Trans. 2010. PMID: 20066236
The 1 : 2 adduct with 2-acetylpyridine parallels its perchlorate analogue, the ligands being bidentate in a mononuclear complex [L(2)AgOSO(2)CF(3)], while adducts of 2,9-dimethylphenanthroline and 2,2'-biquinolyl, both acetonitrile monosolvates, take the form [LAg(NCMe)]tf …
The 1 : 2 adduct with 2-acetylpyridine parallels its perchlorate analogue, the ligands being bidentate in a mononuclear complex [L(2)AgOSO(2 …