An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus yl...

Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction ...

The anionic [2,3] sigmatropic Wittig rearrangements of deprotonated 4-hetera-1-pentenes and the anionic [3,3] sigmatropic Cope rearrangements of 3-substituted-1,5-hexadienes were explored by using density functional theory calculations. While the deprotonated anionic 3-hydroxy-1,5 hexadiene (2a), 3-thiohydroxy-1,5-hexadiene (2c), and 3-formamidyl-1,5-hexadiene (2d) Cope substrates undergo conce...

the synthesis of functionalized 2-oxo-2h-coumarin derivatives has been studied by a one-pot reaction of o-hydroxybenzaldehyde, ethyl 2-bromoacetate and triphenylphosphine in the presence of catalytic amount of triethyl amine in etoac, water or under solvent free conditions. we have found the best results obtained under solvent free condition.

the imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the n-isocyaniminotriphenylphosphorane (ph3pnnc) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. the 1,3,4-oxadiazole derivatives are formed via intramolecular aza-wittig reaction of the iminophosphorane intermediate. the reactions were comp...

The elaboration of the first organophosphorus-catalyzed diaza-Wittig reaction is reported. This catalytic reaction is applied to the synthesis of substituted pyridazine and phthalazine derivatives bearing electron-withdrawing groups with good to excellent yields from substrates containing a diazo functionality as the starting material and a phospholene oxide as the catalyst.

An efficient aqueous Wittig reaction was enabled on protein bioconjugation for the first time. By investigating the reaction on small molecules, peptides, and proteins, a site-specific reaction targeting "aldehyde tag" was presented. A variety of functional groups could be introduced into the protein of interest.