Rhodium-catalyzed synthesis of quinolines and imines under mild conditions

Abstract

An environmentally benign protocol for the synthesis of quinolines in aqueous medium by using Rh(II)acetate/TPPTS recyclable catalytic system has been developed. The anilines were reacted smoothly with allyl alcohols furnishing the corresponding quinolines in moderate to good yields. This 10 catalytic system was recycled up to five runs without much loss in its catalytic activity. Furthermore, imines were also synthesized from benzylamines in moderate to good yields.A simple and efficient protocol for the synthesis of quinolines in aqueous medium by using Rh(II)acetate/TPPTS recyclable catalytic system has been developed. This catalytic system was recycled up to five runs without much loss in its catalytic activity. Furthermore, imines were also synthesized from benzylamines in moderate to good yields under solvent free condition.

Dirhodium: carbene transformations and beyond

“…88 In 2015, Bhanage and coworkers found that the quinolines 157 could be synthesized from anilines and allyl alcohol 156 using Rh 2 (OAc) 4 and tri- phenylphosphine trisulfonate sodium salt (TPPTS) as the catalysts in a simple but efficient manner (Scheme 49). 89 Remarkably, this reaction was conducted in water and the catalyst could be recycled up to five runs without much loss in its catalytic activity. Mechanistically, dirhodium hydride-mediated isomerization of allyl alcohol to the corresponding propanal was involved.…”