Effective BI‐DIME Ligand for Suzuki–Miyaura Cross‐Coupling Reactions in Water with 500 ppm Palladium Loading and Triton X

Abstract

An efficient, sustainable,a nd broadly applicable procedure has been developedf or Suzuki-Miyaura crosscoupling reactions in environmentally benign solvent( water) by employing as little as 500 ppm Pd(OAc) 2 with am onophosphorus BI-DIME ligand in the presence of inexpensive and commercially available nonionic surfactant Triton X-100.This methodw as appliedt oabroad range of functionalized reaction partners, thereby affording excellent yields of the coupling products,i ncluding active pharmaceutical ingredients (APIs). An interesting kinetic study by using reaction calorimetry is also presented, whichd escribes the effect of reaction parameters that enabled the low catalyst loading.

Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles

“…Probably, monofluorinated cyanobiphenyls 6g and 5i are less activated to phenylation by 3 •– than their difluorinated analogues are. Data on 5-fluoro-2-cyanobiphenyl 5g and 4-fluoro-2-cyanobiphenyl 5h can be found in the literature (catalytic cross-coupling was conducted for their synthesis). Because of their small content in the reaction mixtures, we did not isolate these products.…”

A Glimpse into Green Chemistry Practices in the Pharmaceutical Industry

“…Researchers from Boehringer Ingelheim also demonstrated the impact of the reaction medium on reaction outcome . With the use of aqueous Triton X‐100 as a reaction medium and 500 ppm palladium catalyst, the authors synthesized an 11‐β‐HSD1 inhibitor on a multigram scale in excellent yield (Scheme ).…”

Hydrogenation of Itaconic Acid in Micellar Solutions: Catalyst Recycling with Cloud Point Extraction?

“…From the surfactant screening, TX-114, NP5, NP8, and MO 13/50 show a lower CPT and might be suitable for a combined reaction and separation process. Often TX-100 is used as a surfactant in catalytic reactions , with good performance, but the CPT of TX-100 is about three times higher than that of TX-114; therefore, it was not considered in these investigations. As well, MO 13/70 shows a CPT above 70 °C, which is not suitable when the reaction and separation process is combined, since catalyst deactivation could occur at high separation temperatures.…”