Simultaneous control of regioselectivity and enantioselectivity in the hydroxycarbonylation and methoxycarbonylation of vinyl arenes

Abstract

Using a family of novel mononuclear and dinuclear palladium complexes of phanephos ligands, the simultaneous control of regioselectivity and enantioselectivity in the hydroxycarbonylation and alkoxycarbonylation of styrene derivatives has been realised for the first time.

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

“…Enantioselective synthesis of the branched ester 28, from 1-phenoxy-3-vinylbenzene, 25, was also performed using a catalyst developed by Clarke, 30…”

Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids

“…Among the numerous known synthetic methods for their preparation [ 2 , 3 ], the regioselective carbonylation of styrenes provides straightforward and easy access [ 4 ]. Although notable progress has been reported in the enantioselective hydroxycarbonylation of styrenes [ 5 , 6 , 7 ], still, the racemic hydroxy/alkoxy-carbonylation continues to be attractive for the scientific community, too. Here, palladium complexes in the presence of acid represent state-of-the-art catalyst systems for the synthesis of 2-aryl propionic acid.…”

Parameters Influencing Reactivity and Regioselectivity in the Methoxycarbonylation of Arylalkenes

“…The application requirements of linear versus branched products (or vice versa) as well as catalyst life-time also led to the evaluation of a plethora of mono-and bidentate ligands to be used in the catalyst system. [20][21][22][23][24][25][26] During these studies the substituents on the phosphorus atom were varied to evaluate the effect of electron-donating or electron-withdrawing groups attached to the ligand on catalyst activity and selectivity towards the linear product, 14,27,28 as well as towards the preferential formation of the branched product. 29,30 Other studies focused on the use of heterobidentate P,N-donor ligands, [31][32][33] and chelating nitrogen ligands 31,34 as well as the effect of the counterion 14,[16][17][18][19] in this regard.…”