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An efficient approach to decarboxylative C3-acylation of benzothiophenes or benzofurans with α-oxocarboxylic acids via palladium-catalyzed C–H bond activation was developed. This method was compatible with a variety of functional groups and provided an attractive route to 3-acylbenzothiophenes and 3-acylbenzofurans in good to high yields.

An efficient method for synthesis of 1,3-diynes through the CuI/1,10-phenanthroline-catalyzed oxidative decarboxylative homocoupling of aryl pioprolic acids in aqueous DMF has been developed. The catalytic system was suitable for a variety of arylpropiolic acids, and the corresponding 1,3-diynes could be prepared in high yields. The catalytic system was recovered from the organic products by filtration and its aqueous DMF filtrate retained good activity even after at least four cycles of use.

This work reported that Suzuki–Miyaura coupling reactions of arylboronic acid with aryl bromide or iodides were mediated by Pd(OAc)2 and 4-(benzylthio)-N,N,N-trimethylbenzenammonium chloride in the presence of Na2CO3 in water under the mild conditions. The corresponding Suzuki–Miyaura coupling products were obtained in good to excellent yields.

An efficient method of ligand-free Cu-catalyzed oxidative decarboxylative homocoupling of aryl propiolic acids was developed. When CuI was employed as the catalyst and I 2 as the oxidant, the decarboxylative homocoupling reaction for C sp –C sp bond formation in DMSO underwent smoothly to afford the corresponding 1,4-disubstituted 1,3-dialkynes in good to excellent yields without any organic ligands. This catalytic system was applicable to aryl propiolic acids bearing different steric, electronic, and functional groups.