Synthesis of highly substituted diphenylacetamides and diphenylsulfonamides by the goldberg coupling reaction

We report the synthesis and characterisation of multisubstituted diphenylacetamides, diphenylsulfonamides and diphenylamines (and some observations on cyclisation of the last).Fundação para a Ciência e a Tecnologia (FCT)ICCTI and CRUP (Portugal) and the British Council for financial suppor

Nickel–NHC-Catalyzed Cross-Coupling of 2-Methylsulfanylbenzofurans with Alkyl Grignard Reagents

NiCl2(PPh3)(IPr) catalyzes cross-coupling reactions of 2-methylsulfanylbenzofurans with alkyl Grignard reagents. Other nickel complexes such as NiCl2(dppe) failed to catalyze the same reaction. The alkylation is applicable to the synthesis of a couple of protein tyrosine phosphatase inhibitors, 3-(4-biphenylyl)-2-alkylbenzofurans

Nitromethane conjugate addition to 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4Hchromen- 4-ones

Chromone are a group of oxygen-containing heterocycles, which are often associated to important biological activities.1 Chromone derivatives are also seen as interesting scaffolds to input further functionalizations,2 most of them through chemical transformations such as oxidation, condensation, Diels-Alder or conjugate addition. Conjugate addition of carbon nucleophiles to electron-deficient alkenes is one of the most important methods available for carbon–carbon bond-forming reactions. A wide range of carbon nucleophiles easily undergo conjugate addition with various substrates such as chalcones, cinnamylideneacetophenones or styrylchromones. Following previous work of our research group involving the 1,6-conjugate addition of nitromethane to (E)-2- styrylchromones,3 herein we report the first reactivity studies in the nitromethane conjugate addition to the extended unsaturated π-system of 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones 1 (Scheme 1). The DBU catalyzed nitromethane addition reaction afforded the corresponding β-(nitromethyl)chromones 2 (1,6-conjugate addition) as major products. (E)-5'-(Nitromethyl)-3'-styryl-[1,1'-biphenyl]-2-ol 3 and 3'-aryl-2'-nitro-5'-(nitromethyl)spiro [chromane- 2,1'-cyclohexan]-4-one 4 derivatives were also isolated as minor products, which result from the addition of two nitromethane molecules, through tandem processes.info:eu-repo/semantics/publishedVersio

Synthesis and late-stage functionalization of complex molecules through C-H fluorination and nucleophilic aromatic substitution.

We report the late-stage functionalization of multisubstituted pyridines and diazines at the position α to nitrogen. By this process, a series of functional groups and substituents bound to the ring through nitrogen, oxygen, sulfur, or carbon are installed. This functionalization is accomplished by a combination of fluorination and nucleophilic aromatic substitution of the installed fluoride. A diverse array of functionalities can be installed because of the mild reaction conditions revealed for nucleophilic aromatic substitutions (S(N)Ar) of the 2-fluoroheteroarenes. An evaluation of the rates for substitution versus the rates for competitive processes provides a framework for planning this functionalization sequence. This process is illustrated by the modification of a series of medicinally important compounds, as well as the increase in efficiency of synthesis of several existing pharmaceuticals