A method of reducing a C—O bond to the corresponding C—H bond in a substrate, which could be a benzylic alcohol, allylic alcohol, ester or an ether bond beta to a hydroxyl group or alpha to a carbonyl group using a recyclable metal catalyst system. The recyclable catalyst system is also applicable to reducing a C═O bond to the corresponding C—OH bond and then C—H bond. These methodologies can be linked in one-pot to selective oxidation and depolymerizations of aromatic polyols such as lignin.

A method of reducing a C—O bond to the corresponding C—H bond in a substrate, which could be a benzylic alcohol, allylic alcohol, ester or an ether bond beta to a hydroxyl group or alpha to a carbonyl group using a recyclable metal catalyst system. The recyclable catalyst system is also applicable to reducing a C═O bond to the corresponding C—OH bond and then C—H bond. These methodologies can be linked in one-pot to selective oxidation and depolymerizations of aromatic polyols such as lignin.

A method of reducing a C—O bond to the corresponding C—H bond in a substrate, which could be a benzylic alcohol, allylic alcohol, ester or an ether bond beta to a hydroxyl group or alpha to a carbonyl group using a recyclable metal catalyst system. The recyclable catalyst system is also applicable to reducing a C═O bond to the corresponding C—OH bond and then C—H bond. These methodologies can be linked in one-pot to selective oxidation and depolymerizations of aromatic polyols such as lignin.

A fragrance precursor represented by the formula 1

##STR00001##

wherein

X and Y together represent a double bond to a carbon atom bearing R.sub.1 and R.sub.2, with R.sub.1═H, methyl, acetyl or C.sub.1—C.sub.3 alkoxycarbonyl (e.g. ethoxycarbonyl); and R2=phenyl optionally substituted with up to 3 (i.e. 0, 1, 2 or 3) groups selected from C.sub.1—C.sub.4 alkyl (e.g. methyl, ethyl, iso-propyl, tert-butyl), vinyl, hydroxy, C.sub.1—C.sub.3 alkoxy (e.g. ethoxy), and —O—CH.sub.2—O—, e.g. R.sub.2 is benzo[d][1,3]dioxol-5-yl, 4-methylphenyl, 4-methoxyphenyl, 4-vinylphenyl or 3-ethoxy-4-hydroxyphenyl or

R2=naphthyl, (naphthyl) methyl, 1,1,2,4,4,8-hexamethyl-1,2,3,4-tetrahydronaphthalen-7-yl, or 1,1,2,4,4,-penta methyl-1,2,3,4-tetrahydronaphthalen-7-yl or

R2=COR3, wherein R3 is H, C1-C10 alkoxy (e.g. ethoxy, 1-(3,3-dimethylcyclohexyl)ethoxy), C1-C4 alkyl (e.g. methyl, ethyl, propyl, iso-propyl, tert-butyl), e.g. R2 is formyl, acetyl, ethoxycarbonyl, 1-(3,3-dimethylcyclohexyl)ethoxycarbonyl; or wherein

X is OR4, with R4 being H or alkyl, and

Y is OR5, with R5 being alkyl,

useful as a perfume ingredient.

A fragrance precursor represented by the formula 1

##STR00001##

wherein

X and Y together represent a double bond to a carbon atom bearing R.sub.1 and R.sub.2, with R.sub.1═H, methyl, acetyl or C.sub.1—C.sub.3 alkoxycarbonyl (e.g. ethoxycarbonyl); and R2=phenyl optionally substituted with up to 3 (i.e. 0, 1, 2 or 3) groups selected from C.sub.1—C.sub.4 alkyl (e.g. methyl, ethyl, iso-propyl, tert-butyl), vinyl, hydroxy, C.sub.1—C.sub.3 alkoxy (e.g. ethoxy), and —O—CH.sub.2—O—, e.g. R.sub.2 is benzo[d][1,3]dioxol-5-yl, 4-methylphenyl, 4-methoxyphenyl, 4-vinylphenyl or 3-ethoxy-4-hydroxyphenyl or

R2=naphthyl, (naphthyl) methyl, 1,1,2,4,4,8-hexamethyl-1,2,3,4-tetrahydronaphthalen-7-yl, or 1,1,2,4,4,-penta methyl-1,2,3,4-tetrahydronaphthalen-7-yl or

R2=COR3, wherein R3 is H, C1-C10 alkoxy (e.g. ethoxy, 1-(3,3-dimethylcyclohexyl)ethoxy), C1-C4 alkyl (e.g. methyl, ethyl, propyl, iso-propyl, tert-butyl), e.g. R2 is formyl, acetyl, ethoxycarbonyl, 1-(3,3-dimethylcyclohexyl)ethoxycarbonyl; or wherein

X is OR4, with R4 being H or alkyl, and

Y is OR5, with R5 being alkyl,

useful as a perfume ingredient.

A solid-supported catalyst ligand which chelates palladium (II) species to form a complex that functions as a heterogeneous catalyst that is stable and can be recycled without significantly losing any catalytic activity in a variety of chemical transformations, a method for producing the solid-supported catalyst ligand and a method for catalyzing a palladium cross-coupling reaction, such as the Suzuki-Miyaura, Mizoroki-Heck, and Sonagashira reactions.

A solid-supported catalyst ligand which chelates palladium (II) species to form a complex that functions as a heterogeneous catalyst that is stable and can be recycled without significantly losing any catalytic activity in a variety of chemical transformations, a method for producing the solid-supported catalyst ligand and a method for catalyzing a palladium cross-coupling reaction, such as the Suzuki-Miyaura, Mizoroki-Heck, and Sonagashira reactions.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.

The present disclosure relates to HIF-2α inhibitors and methods of making and using them for treating cancer. Certain compounds were potent in HIF-2α scintillation proximity assay, luciferase assay, and VEGF ELISA assay, and led to tumor size reduction and regression in 786-O xenograft bearing mice in vivo.