Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?

Abstract

The Suzuki cross coupling with phenylboronic acid in the presence of the Pd(OAc) 2 /K 3 PO 4 /DMF catalytic system was successful for aryl bromides and somewhat poorer for aryl chlorides. Addition of 1,3 bis(tetrazol 1 yl)benzene or its analogs lowered the yields of biaryls.

Synthesis and structure of novel benzisothiazole-tetrazolyl derivatives for potential application as nitrogen ligands

“…Indeed, it has been shown that the tetrazole ligand is able to participate in at least seven distinct types of coordination modes with metal ions, in the construction of novel metal-organic frameworks. Furthermore, numerous tetrazolyl ligands, coordinated with different metal centres, such as nickel, ruthenium, palladium or platinum, have been tested in catalyzed reactions [18][19][20].…”

Transition-Metal-Catalyzed Site-Selective Cross-Coupling of Di- and Polyhalogenated Compounds

“…Zlotin and co-workers described an ortho-preference in the cross-coupling of polychlorophenyl ketones with phenylboronic acid, although the selectivity was not very high (Scheme 82). 86 Scheme 82 Cross-coupling of dichloroacetophenone with phenylboronic acid…”

One-pot synthesis of substituted styrenes from vicinal dibromoalkanes and arylboronic acids

“…The reactions in DME-[bmim]BF 4 (see Experimental, method А) proceeded chemoselectively with the formation of cross coupling products, whereas in DMF (method B, see Ref. 10), according to chromato mass spectrometry data, the formation of considerable amount of biaryls (due to homodimerization of arylboronic acids) and dienes (due to homodimerization of alkenyl bromides) was ob served. The preparative experiments were carried out ac cording to method А, the main reaction products were identified by GC MS and 1 H and 13 C NMR spectra.…”