5100-57-2Relevant academic research and scientific papers
Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands
Hu, Zhiyong,Wei, Xiao-Jing,Handelmann, Jens,Seitz, Ann-Katrin,Rodstein, Ilja,Gessner, Viktoria H.,Goo?en, Lukas J.
supporting information, p. 6778 - 6783 (2021/02/01)
The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.
Studies on Pyrimidine Derivatives. XXXVIII. Cross-Coupling Reaction of N-Heteroaryl Iodides with Ethoxycarbonylmethylzinc Bromide in the Presence of Palladium Catalyst
Yamanaka, Hiroshi,An-naka, Masayuki,Kondo, Yoshinori,Sakamoto, Takao
, p. 4309 - 4313 (2007/10/02)
In the presence of tetrakis(triphenylphosphine)palladium, 2-iodo-4,6-dimethylpyrimidine and 4-iodo-2,6-dimethylpyrimidine reacted with ethoxycarbonylmethylzinc bromide (Reformatsky reagent) to give ethyl 4,6-dimethyl-2-pyrimidineacetate and ethyl 2,6-dimethyl-4-pyrimidineacetate, respectively.In contrast, the reaction of 5-iodo-2,4-dimethylpyrimidine with the same reagent resulted in recovery of the starting iodide.Similar results were observed in the reactions of various N-heteroaryl iodides.Keywords - Reformatsky reagent; cross-coupling reaction; N-heteroaryl halide; N-heteroarylacetic acid; palladium catalyst; ethyl bromoacetate
