Abstract In the last decade, a number of metal‐catalyzed technologies for functionalization C−H bonds in carbonaceous aromatic substrates have been developed. However, similar reactions with aza‐heteroaromatic precursors are more challenging and much less Herein, we report first time catalytic formal cycloadditions N,S ‐heterocycles featuring carboxylic acid substituents, unsaturated partners (...

The Ni-catalyzed reaction of aromatic amides with alkynes in the presence of KOBu involves C–H/N–H oxidative annulation to give 1(2H)-isoquinolinones. A key to the success of the reaction is the use of a catalytic amount of strong base, such as KOBu. The reaction shows a high functional group compatibility. The reaction with unsymmetrical alkynes, such as 1-arylalkynes, gives the corresponding ...

A mild, efficient and LiCl-free synthetic method for indole derivatives based on the heteroannulation of alkynes with 2-iodoanilines was achieved using palladium on carbon (Pd/C) and NaOAc in heated NMP. The N-tosyl protection of 2-iodoaniline expedited the reaction progress, while other protecting groups, such as tert-butoxycarbonyl, acetyl, and benzyloxycarbonyl groups, underwent deprotection...

Electrochemical procedures present a selective and environmentally friendly approach for fine chemicals preparation. The use of electricity instead classical chemical reagents is economical ecologically attractive. In fact, from renewable resources can be used electrochemical transformations with highly sustainable desirable applications. Alkynes triple C?C bond has key role in many transformat...

We report the use of cationic gold complexes [Au(NHC)(CH3CN)][BF4] and [{Au(NHC)}2(μ-OH)][BF4] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows...

We report the development of a multicatalytic, one-pot, asymmetric Michael/Stetter reaction between salicylaldehydes and electron-deficient alkynes. The cascade proceeds via amine-mediated Michael addition followed by an N-heterocyclic carbene-promoted intramolecular Stetter reaction. A variety of salicylaldehydes, doubly activated alkynes, and terminal, electrophilic allenes participate in a o...

The addition of bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me4)] to α,β-unsaturated carbonyl compounds giving β-boryl carbonyl compounds and the addition to terminal alkynes yielding either 2-boryl-1-alkenes or 1-boryl-1-alkenes were carried out in DMF at room temperature in the presence of CuCl and AcOK. The transmetalation between diboron and [Cu(Cl)OAc]K generating a borylcopper species was pr...

A novel palladium-catalyzed intermolecular aminopalladation/C-H activation method for selectively synthesizing (E)-(2-oxindolin-3-ylidene)phthalimides has been developed. In the presence of Pd(OAc)2 and PhI(OAc)2, alkynes were difunctionalized with a phthalimide and an arene sp2 C-H bond to selectively synthesize (E)-(2-oxoindolin-3-ylidene)phthalimides, which products are of great potential ph...

Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)₂•H₂O/DBU is described. Various benzamide substituents, ring substitutions, including heteroaryl, aryl acetylenes and aliphatic alkynes, could be applied to afford the desired products in good to moderate yield with high stereoselectivity. It is noteworthy...

A straightforward synthetic methodology for the preparation of photochromic siloles based on dithienylethene motif is developed. It relies upon an efficient palladium-catalyzed annulation reaction a 2,3-bis(3-thienyl)-silirene with terminal alkynes in mild conditions. The functional group-tolerant and can be performed high yields variety alkynes. even extended to polymeric polypropargylmethacry...