This invention relates to a process for producing electron deficient olefin precursors, such as 2-cyanoacetates, using an acid catalyzed transesterification reaction.

This invention relates to a process for producing electron deficient olefins, such as 2-cyanoacrylates, using an acid catalyzed Knoevenagel condensation reaction.

Catalytic hydroesterification of alkyl lactates give alkyl 2-(propionyloxy)propanoates, starting from alkyl lactate, carbon monoxide, ethylene gas, and a palladium catalyst. Pyrolysis of alkyl 2-(propionyloxy)propanoates gives acrylate esters.

Lewis acidic metal-organic framework (MOF) materials comprising triflate-coordinated metal nodes are described. The materials can be used as heterogenous catalysts in a wide range of organic group transformations, including Diels-Alder reactions, epoxide-ring opening reactions, Friedel-Crafts acylation reactions and alkene hydroalkoxylation reactions. The MOFs can also be prepared with metallated organic bridging ligands to provide heterogenous catalysts for tandem reactions and/or prepared as composites with support particles for use in columns of continuous flow reactor systems. Methods of preparing and using the MOF materials and their composites are also described.

Methods of CH bond fluorination using non-heme manganese catalyst are described herein. For example, a method comprises providing a reaction mixture including a non-heme manganese catalyst, a substrate comprising an sp.sup.3 CH bond and a fluorinating agent and converting the sp.sup.3 CH bond to a CF bond in the presence of the non-heme manganese catalyst or a derivative thereof.

Methods for preparing the Bruton's Tyrosine Kinase (BTK) inhibitor compound 2-{3-hydroxymethyl-1-methyl-5-[5-((S)-2-methyl-4-oxetan-3-yl-piperazin-1-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-[3,4]bipyridinyl-2-yl}-7,7-dimethyl-3,4,7,8-tetrahydro-2H,6H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one are provided.

Methods for preparing the Bruton's Tyrosine Kinase (BTK) inhibitor compound 2-{3-hydroxymethyl-1-methyl-5-[5-((S)-2-methyl-4-oxetan-3-yl-piperazin-1-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-[3,4]bipyridinyl-2-yl}-7,7-dimethyl-3,4,7,8-tetrahydro-2H,6H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one are provided.

Provided is a method for producing a protected glycoside derivative, including reacting a sugar in which all hydroxyl groups of the sugar are protected by protective groups and protective groups of a hydroxyl group at a 1-position and a hydroxyl group at a 2-position are acyl groups, with a phenolic compound in the presence of at least one catalyst selected from the group consisting of trifluoromethanesulfonic acid and copper (II) trifluoromethanesulfonate, in which the phenolic compound is bonded to an anomeric position of the sugar and other hydroxyl groups of the sugar are protected.