Synthesis and Structure of 2,2'-Dihydroxybenzophenones and 1,8-Dihydroxyfluorenones

Sharma, Vijay; Bachand, Benoit; Simard, Michel; Wuest, James D.

doi:10.1021/jo00104a040

Cited by 23 publications

(25 citation statements)

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“…The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b01639. Experimental procedures; compound characterization data; 1 H, 13 C{ 1 H}, 31 P{1H} and 2D NMR spectra; and crystal data of Rh(CO)(acac)(L4) (PDF)…”

Section: * S Supporting Informationmentioning

confidence: 99%

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Ligand-Controlled Direct Hydroformylation of Trisubstituted Olefins

Shin

Kim

et al. 2019

Org. Lett.

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The direct hydroformylation of trisubstituted olefins has been achieved with a combination of a Rh(I) catalyst and a π-acceptor phosphorus (briphos) ligand. A sterically bulky briphos ligand with a large cone angle that forms a 1:1 complex with Rh(I) is found to be reactive for the hydroformylation of trisubstituted olefins. The aldehyde products were obtained with high diastereoselectivity (>99:1) and regioselectivity (49%–81%).

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Section: * S Supporting Informationmentioning

confidence: 99%

“…In order to enhance the steric repulsion, we newly prepared briphos ligands with tert -butyl groups at the ortho and para positions of the phenol rings, as shown in Scheme . The three-straightforward-step reactions from compound 1 , imine formation, reduction, and phosphoramidite formation, gave briphos ligands L1 – L4 in overall yields of 23%–68%.…”

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confidence: 99%

Ligand-Controlled Direct Hydroformylation of Trisubstituted Olefins

Shin

Kim

et al. 2019

Org. Lett.

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“…Found: C, 77.0; H, 8. 4 J HH = 2.25 Hz, Ar-H), 3.71 (sept., 2H, 3 J HH = 6.72 Hz, CH(CH 3 ) 2 ), 3.19 (sept., 2H, 3 J HH = 6.78 Hz, CH(CH 3 ) 2 ), 2.93 (br sept, 4H, 3 J HH not observable, CH(CH 3 ) 2 ), 1.86 (s, 6H, Me), 1.55-1.15 (br m, 36H, 3 J HH not observable, CH(CH 3 ) 2 ), 1.08 (d, 6H, 3 J HH = 6.91 Hz, CH(CH 3 ) 2 ), 0.96 (d, 6H, 3 J HH = 6.76 Hz, CH(CH 3 ) 2 ).…”

Section: Preparation Of the Bis(imino)phenol Ligand (I)mentioning

confidence: 99%

“…In particular, for 2,2′-dihydroxybenzophenone (D) and 2,7-disubstituted-1,8-biphenylenediol (E) derived complexes, the carbonyl group is rendered more susceptible to attack by incoming nucleophiles. 4 Previous coordination studies of bis(imino)phenoxide ligands are restricted to transition metal systems: rhenium complexes containing the sterically less hindered ligands (R = C 6 H 5 , C 6 H 4 OMe-p and C 6 H 4 Cl-p), 5 and more recently cobalt and nickel oligomerisation precatalysts (R =…”

Section: Introductionmentioning

confidence: 99%

Bis(imino)phenoxide complexes of aluminium

et al. 2004

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Reaction of Me(3)Al (one equivalent) with the bis(imino)phenol, [2,6-(ArNCH)(2)-4-MeC(6)H(2)OH] (I)(Ar = 2,6-Pr(i)(2)C(6)H(3)) in toluene at ambient temperature yields the yellow complex [Me(2)Al[2,6-(ArNCH)(2)-4-MeC(6)H(2)O]](1). Interaction of two equivalents of Me(3)Al in refluxing toluene affords the red complex [(Me(2)Al)(2)[2-ArNCH(Me)-6-(ArNCH)-4-MeC(6)H(2)O]](2). Similar interaction (two equivalents, refluxing toluene) of MeAlCl(2) or (i)Bu(3)Al with [2,6-(ArNCH)(2)-4-MeC(6)H(2)OH] affords [ClAl[2,6-(ArNCH)(2)-4-MeC(6)H(2)O](2)](3) or [(i)Bu(2)Al[2,6-(ArNCH)(2)-4-MeC(6)H(2)O]](4), respectively. Hydrolysis of 2 readily affords the iminoaminophenol ligand [2-(ArN=CH)-6-ArNHCH(Me)-4-MeC(6)H(2)OH](II), which reacts further with Me(3)Al to afford [Me(2)Al[2-ArNCH(Me)-6-(ArNCH)-4-MeC(6)H(2)O]](5). An X-ray study on reveals bidentate imino-alkoxide ligation about the distorted aluminium centre, whereas is a binuclear structure with tetrahedral aluminiums ligated by imino-alkoxide and amido-alkoxide ligand fragments, respectively. For and bidentate imino-alkoxide ligation is observed.

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“…can induce large distortions in some bond angles of the molecule (33)(34)(35). The result of such distortions is to create torque in the enzyme-substrate complex, thus, altering the reaction rate catalyzed by the enzyme.…”

Section: Am1 Molecular Mechanics Calculationsmentioning

confidence: 99%