Yasuyuki Koie

Palladium-catalyzed synthesis of triarylamines from aryl halides and diarylamines

Abstract Various triarylamines can be readily prepared in excellent yields by palladium-catalyzed cross-coupling reaction of aryl halides and diarylamines. The amination reaction takes place rapidly by using the catalyst combination of Pd(OAc) 2 and a bulky and electron-rich ligand. P( t -Bu) 3 .

Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst

A PdP(t-Bu)3 catalyst system has revealed very high activity and selectivity for the amination of N-(hetero)aryl halides with unprotected piperazine. A wide variety of N-(hetero)arylpiperazines could be prepared using this catalyst. Turnover numbers up to 6400mol/mol have been obtained.

Palladium/P(t-Bu)3-catalyzed synthesis of N-aryl azoles and application to the synthesis of 4,4′,4′′-tris(N-azolyl)triphenylamines

Abstract Palladium/P( t -Bu) 3 catalyzed the coupling of aryl halides with azoles such as pyrrole, indole, and carbazole, effectively. K 2 CO 3 and Rb 2 CO 3 worked very well as bases, whereas Cs 2 CO 3 and t -BuONa gave only trace yields of products. Triazolyl compounds such as TCTA were also synthesized.

PalladiumP(t-Bu)3-catalyzed synthesis of aryl t-butyl ethers and application to the first synthesis of 4-chlorobenzofuran

PdP(t-Bu)3 catalyzed reaction of aryl halides with sodium t-butoxide effectively to give aryl t-butyl ethers. The high catalytic activity realized the formation of aryl t-butyl ethers from not only electron-deficient aryl halides but also electron-rich aryl halides. Moreover, the first synthesis of 4-chlorobenzofuran was attained utilizing the selective mono-t-butoxylation of aryl dihalide.