914922-76-2

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 106-37-6 1.4-dibromobenzene 
• 139139-81-4 bis(4-bromophenyl)iodonium triflate 

Downstream Products

• 914922-77-3 (1S)-1,5-anhydro-2,3,4,6-tetra-o-benzyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-D-glucitol 

Relevant academic research and scientific papers

Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C -Glycosides of Biomedical Relevance

A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis of aryl C-glycosides is reported. This process capitalizes on a stereoretentive reaction of configurationally stable C1 stannanes and is promoted by a palladium catalyst in the presence of a bulky phosphine ligand that suppresses the undesired β-elimination. The utility of this reaction has been demonstrated in the preparation of a series of C-glycosides derived from common saccharides resulting in exclusive transfer of anomeric configuration from the anomeric nucleophile to the product, and in the synthesis of empagliflozin, a commercial antidiabetic drug.

Nickel-Catalyzed Asymmetric Friedel-Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group

The nickel-catalyzed highly enantioselective Friedel-Crafts propargylation of 3-substituted indoles with propargylic carbonates bearing an internal alkyne group was developed. A wide array of the propargylic carbonates as well as 3-substituted indoles can be applicable to the asymmetric nickel catalysis, providing the corresponding chiral C-3 propargylated indolenine derivatives bearing two vicinal chiral centers in up to 89% yield with up to >99% ee and 94:6 dr (24 examples).

NaBArF4-Catalyzed Oxidative Cyclization of 1,5- and 1,6-Diynes: Efficient and Divergent Synthesis of Functionalized γ- and δ-Lactams

An efficient NaBArF4-catalyzed oxidative cyclization of readily available 1,5- and 1,6-diynes has been developed. Importantly, this transition metal-free oxidative catalysis proceeds via a presumable Lewis acid-catalyzed SN2’ pathway, which is distinct from the relevant oxidative rhodium and gold catalysis. This method leads to the facile and practical construction of a diverse range of synthetically useful γ- and δ-lactams in mostly good to excellent yields with broad substrate scope.

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides

Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.

DIPHENYLHETEROCYCLE CHOLESTEROL ABSORPTION INHIBITORS

Various azetidinone, pyrrolidine, imidazolidine, and oxazolidine derivatives are described, as are pharmaceutical compositions containing these compounds and methods of treatment of diseases using these compounds. Other embodiments are also described.