cas 36282-40-3, 3-METHOXYPHENYLMAGNESIUM BROMIDE

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Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information
p. 19257 - 19262
(2019/12/02)

Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents
A simple protocol for performing chromium-catalyzed highly diastereoselective alkylations of arylmagnesium halides with cyclohexyl iodides at ambient temperature has been developed. Furthermore, this ligand-free CrCl2 enables efficient electrophilic alkenylations of primary, secondary, and tetiary alkylmagnesium halides with readily available alkenyl acetates. Moreover, this chemoselective C-C coupling reaction with stereodefined alkenyl acetates proceeds in a stereoretentive fashion. A wide range of functional groups on alkyl iodides and alkenyl acetates are well tolerated, thus furnishing functionalized Csp2-Csp3 coupling products in good yields and high diastereoselectivity. Detailed mechanistic studies suggest that the in situ generated low-valent chromium(I) species might be the active catalyst for these Csp2-Csp3 cross-couplings.
Li, Jie,Ren, Qianyi,Cheng, Xinyi,Karaghiosoff, Konstantin,Knochel, Paul
supporting information
p. 18127 - 18135
(2019/11/19)

Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates
Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.
Eno, Meredith S.,Lu, Alexander,Morken, James P.
supporting information
p. 7824 - 7827
(2016/07/11)

Facile Hydrogenolysis of C(sp3)–C(sp3) σ Bonds
The modification of benzylic quaternary, tertiary, and secondary carbon centers through palladium-catalyzed hydrogenolysis of C(sp3)–C(sp3) σ bonds is presented. When benzyl Meldrum's acid derivatives bearing quaternary benzylic centers are treated under mild hydrogenolysis conditions – palladium on carbon and atmospheric pressure of hydrogen – aromatics substituted with tertiary benzylic centers and Meldrum's acid are obtained with good to excellent yield. Analogously, substrates containing tertiary or secondary benzylic centers yield aromatics substituted with secondary benzylic centers or toluene derivatives, respectively. Furthermore, this strategy is used for the high yielding synthesis of diarylmethanes. The scope of the reductive dealkylation reaction is explored and the limitations with respect to steric and electronic factors are determined. A mechanistic analysis of the reaction is described that consisted of deuterium labelling experiments and hydrogenolysis of enantioenriched derivatives. The investigation shows that the C(sp3)–C(sp3) σ bond-cleaving events occur through a hybrid SN1/SN2 mechanism, in which the palladium center displaces a carbon-based leaving group, namely Meldrum's acid, with inversion of configuration, followed by reductive elimination of palladium to furnish a C?H bond. (Figure presented.).
Fillion, Eric,Beaton, Eric,Nguyen, Yen,Wilsily, Ashraf,Bondarenko, Ganna,Jacq, Jér?me
supporting information
p. 3422 - 3434
(2016/11/13)

Use of73Ge NMR Spectroscopy and X-ray Crystallography for the Study of electronic interactions in substituted tetrakis(phenyl)-, -(phenoxy)-, and -(thiophenoxy)germanes
NMR chemical shifts of 1H, 13C, and 73Ge, molecular modeling, and single-crystal X-ray diffraction results are reported for a series of substituted tris- and tetrakis(phenyl)germanes of the type (XC6H4)3GeY and (XC6H 4)4Ge, where X = o-, m-, and p-OCH3, o-, m-, and p-OC2H5, m- and p-CF3, H, p-C(CH 3)3, p-Cl; and Y = Cl and H. Chemical shifts and X-ray data are also reported for o-CH3 and o-OCH3 tetrakis(phenoxy)- ((XC6H4O)4Ge) and thiophenoxygermanes ((XC6H4S)4Ge). For tetrakis derivatives, 73Ge resonances are observed for all but the o-methoxyphenoxy compound, for which the inability to detect a resonance is attributed to rapid quadrupolar relaxation caused by intramolecular interactions of the methoxy oxygen with the central atom. The observation of a relatively broad, slightly upfield 73Ge resonance in the analogous phenyl and thiophenoxy derivatives suggests, as do the results of molecular modeling, that in these compounds there is some hypercoordination. The solid-state structures show bond angles at the aromatic carbon bearing the alkoxy group that suggest an interaction of the alkoxy oxygen with germanium. Oxygen-germanium bond distances are about 17% shorter than the sum of the van der Waals radii.
Yoder, Claude H.,Agee, Tamara M.,Griffith, Allison K.,Schaeffer Jr., Charles D.,Carroll, Mary J.,Detoma, Alaina S.,Fleisher, Adam J.,Gettel, Cameron J.,Rheingold, Arnold L.
experimental part
p. 582 - 590
(2010/04/25)

SUBSTITUTED CYCLOHEXANOLS
Disclosed herein are substituted cyclohexanol opioid receptor modulators and/or neurotransmitter reuptake modulators of Formula I or Formula II, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 33

(2009/02/11)

BENZOQUINAZOLINE DERIVATIVES AND THEIR USE IN TREATING BONE DISORDERS
A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof, wherein the groups R2, R3, R4, Q, X and Y are as defined in the specification, is useful in the treatment of bone conditions related to increased calcium depletion or resorption.
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Page/Page column 107-108

(2008/06/13)

Fungicidal use of phenolic aromatic compounds
A plant fungicide method comprises applying to the locus of a plant pathogen a fungicidally effective amount of a compound of formula (I) STR1 or a salt or a complex thereof, wherein: R1, R2, R3, R4, R5, R6, R7, and R8 are independently H, halo, NO2, (C1 -C4) alkyl, or halo(C1 -C4) alkyl; R3', R4', R5', R3", R4", and R5" are independently H, halo, OH, or CH3, provided that at least one is OH; R6 ' and R6 " are independently H or OH.
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(2008/06/13)

Novel 3-keto-19-nor-Δ4,9 -steroids
Novel 3-keto-19-nor-Δ4,9 -steroids of the formula STR1 wherein R1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, halogen, --CF3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms optionally oxidized to the sulfoxide or sulfone, R2 is selected from the group consisting of methyl and ethyl, R3 is selected from the group consisting of hydrogen, optionally substituted alkyl of 1 to 6 carbon atoms, optionally substituted alkenyl and alkynyl of 2 to 6 carbon atoms, --OH, acetyl, hydroxyacetyl, carboxyalkoxy of 2 to 4 carbon atoms optionally esterified or salified and hydroxyalkyl of 1 to 6 carbon atoms optionally esterified, R4 is selected from the group consisting of hydrogen, alkylthio and alkoxy of 1 to 12 carbon atoms, trialkylsilyl of 1 to 6 carbon atoms, --CN, --OH and alkyl, alkenyl and alkynyl of up to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen and alkylamino and dialkylamino of 1 to 6 alkyl carbon atoms, R5 is selected from the group consisting of hydrogen and methyl in the α- or β-position, X is =0 or hydroxyimino or alkoxyimino of 1 to 4 carbon atoms in the syn or anti form and A and B are an epoxy or a second bond in the 9(10) position and their non-toxic, pharmaceutically acceptable acid addition salts where R4 is an amino group, with the proviso that A and B are not a second bond in the 9(10)-position when X is =0 and R5 is hydrogen and a) R2 is methyl and α) R3 is --OH and i) R1 is ethyl or phenyl and R4 is hydrogen or ii) R1 is ethyl, propyl, isopropyl, vinyl, allyl, isopropenyl, phenyl, 4-fluorophenyl, methoxyphenyl or thienyl and R4 is ethynyl or iii) R1 is propyl, isopropyl, vinyl, allyl, isopropenyl, 4-methoxyphenyl or thienyl and R4 is methyl and β) R3 is acetyl and i) R1 is ethyl, vinyl or phenyl and R4 is --OH or ii) R1 is vinyl and R4 is methyl and b) R2 is ethyl and R1 is vinyl, R3 is --OH and R4 is hydrogen possessing a remarkable antiglucocorticoidal activity.
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(2008/06/13)

FUSED BENZAZEPINES, COMPOSITIONS OF, AND MEDICAL USE THEREOF
Disclosed are fused benzazepine compounds, pharmaceutical compositions including such compounds, methods of using such compounds, for example, in the treatment of psychoses and/or depression, and intermediates useful in the preparation of such compounds.
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(2008/06/13)