Highly Flexible Synthesis of 2-Arylethylamine Derivatives

Abstract

A new and highly flexible procedure for the synthesis of 2-arylethylamine derivatives is described. By the new procedure, the target compounds can be synthesized with high diversity in three steps from aryl halides, terminal alkynes, and primary amines. The reaction sequence starts with a palladium-catalyzed coupling of an aryl halide and a terminal alkyne (Sonogashira coupling). A subsequent Cp 2 TiMe 2 -cata-

Current methods for the synthesis of 2-substituted azoles

“…[110][111][112][113][114] Evans and Bach have utilized a Sonogashira coupling for the preparation of histidine derivatives (Scheme 48) wherein the diiodide 107 undergoes selective coupling as well as dehalogenation in the presence of excess phenylacetylene. 115 Imidazole derivatives (Scheme 49) 116 and thiazole analogs [117][118][119][120][121][122] have been investigated, and regioselective alkynylation is often feasible (Scheme 50). 117 Oxazolyl and thiazolyl triflates have also been shown to be effective substrates 123 …”

Development of the Ti-Catalyzed Intermolecular Hydroamination of Alkynes

“…The goal of this project was the development of a new and highly flexible procedure for the synthesis of a wide variety of 2-arylethylamine derivatives, 29 a class of compounds that is of considerable interest for medicinal chemistry. Some important 2-arylethylamines are shown in Scheme 33.…”

Cross‐Coupling Reactions on Azoles with Two and More Heteroatoms

“…With simple 2-bromothiazole, moderate to good yields have been reported with a number of different alkynes by using conventional catalyst systems [134][135][136] or the relatively new Tedicyp [all-cis-1,2,3,4-tetrakis(diphenylphosphanylmethyl)cyclopentane] ligand. With simple 2-bromothiazole, moderate to good yields have been reported with a number of different alkynes by using conventional catalyst systems [134][135][136] or the relatively new Tedicyp [all-cis-1,2,3,4-tetrakis(diphenylphosphanylmethyl)cyclopentane] ligand.…”

“…Especially 2-bromothiazoles have been used in the Sonogashira reaction. With simple 2-bromothiazole, moderate to good yields have been reported with a number of different alkynes by using conventional catalyst systems [134][135][136] or the relatively new Tedicyp [all-cis-1,2,3,4-tetrakis(diphenylphosphanylmethyl)cyclopentane] ligand. [137] The Sonogashira reaction of 4-bromothiazoles was also reported for example in the synthesis of epothilone C analogs.…”