Naphthalene-modified oligonucleotides have been synthesized and characterized with respect to electron transfer chemistry. Using the Sonogashira coupling reaction, naphthalene can be covalently anchored onto a modified uridine through an ethynyl linkage. This tethering allows for effective electronic coupling with the DNA bases, resulting in a significant red shift of the absorption bands of th...

A general and convenient palladium-catalyzed Sonogashira reaction of in situ generated arenediazonium salts has been developed and various internal arylalkynes are produced in good yields under mild conditions.

Negative-ion electrospray ionisation mass spectrometry with an anionic phosphine ligand enables detection of key intermediates in the Sonogashira reaction. MS/MS techniques are used to generate a Hammett plot for the key reductive elimination step.

The consideration of discrete variables (e.g. catalyst, ligand, solvent) in experimental self-optimization approaches remains a significant challenge. Herein we report the application new mixed variable multi-objective optimization (MVMOO) algorithm for chemical reactions. Coupling MVMOO with an automated continuous flow platform enabled identification trade-off curves different performance cri...

Transition-metal-catalyzed [4+2] heteroannulation of α,β-unsaturated oximes and their derivatives with alkynes has been developed into a powerful strategy for the synthesis pyridines. It nevertheless lacks regioselectivity when unsymmetrically substituted are used. We report herein unprecedented polysubstituted pyridines by formal [5+1] two readily accessible building blocks. A copper-catalyzed...

Simple, straightforward and optimized procedures for preparing extended pi-conjugated linkers are described. Either unsubstituted or 4-donor substituted pi-linkers bearing a styryl, biphenyl, phenylethenylphenyl, and phenylethynylphenyl pi-conjugated backbone are functionalized with boronic pinacol esters as well as with terminal acetylene moieties allowing their further use as building blocks ...

A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV nat...

π-Conjugated microporous networks have been prepared from the tetraarylated diketopyrrolo[3,4-c]pyrrole unit as a tetrafunctional building block. The reactions are carried out using microwave-assisted Yamamoto or Sonogashira cross-coupling. Red insoluble powders are obtained, showing intense fluorescence. The polymer networks exhibit a high gas storage capability, with BET surface areas up to a...

An unreported product outcome from an intended Sonogashira coupling is presented. The generality of this finding has been demonstrated by screening of a range of pre-catalysts. Mechanistic studies are consistent with the tetra-aryl benzene product forming by interception of the aryl halide oxidative addition intermediate by repeated acetylene insertion.

The preparation of functionalized 1,3-enynes bearing an acetal moiety at the 2-position has been studied through Sonogashira reaction bromovinyl acetals with various alkyl- and aryl-substituted terminal alkynes.