In 2022,Gangadhar, Maram; Ramesh, Vankudoth; Prasad, Vadla Shiva; Adiyala, Praveen Reddy published an article in Journal of Organic Chemistry. The title of the article was 《Silver Ions Promoted Palladium-Catalyzed Inactive β-C(sp3)-H Bond Arylation in Batch and Continuous-Flow Conditions》.Computed Properties of C7H5IO The author mentioned the following in the article:
A palladium(II)-catalyzed protocol for inactive β-C(sp3)-H bond functionalization has been first accomplished. The reaction proceeds through five-membered carbocycles for the formation of C-C bonds via the Pd(II)/Pd(IV) cycle. This reaction was carried out with various aryl iodides RI (R = Ph, 9H-fluoren-2-yl, 3,5-di(trifluoromethyl)phenyl, etc.) and benzothiazoles/benzoxazoles/benzimidazoles I (X = S, O, NCH2Ph, etc.; R1 = H, 6-NO2, 5-NO2; R = H), which were well-tolerated in this reaction and successfully generated β-C(sp3)-H arylated products I. Further implementation of this batch protocol to continuous flow by utilizing a PTFE (polytetrafluoroethylene) capillary reactor enhanced the reaction efficiency and decreased the reaction time (18.4 min) as compared to batch conditions (8 h). Even on the gram scale, the process produced excellent yield with negligible diarylations. Functional group tolerance, a continuous-flow approach, and easy-to-handle reaction conditions make this inactive β-C(sp3)-H bond functionalization protocol very attractive. The experimental part of the paper was very detailed, including the reaction process of 4-Iodobenzaldehyde(cas: 15164-44-0Computed Properties of C7H5IO)
4-Iodobenzaldehyde(cas: 15164-44-0) is used in synthesis of 4-[2-(trimethylsilyl)ethynyl]benzaldehyde, 5,15-dimesityl-10-(3-[2-(trimethylsilyl)ethynyi]phenyl}-20-(4-iodophenyl)porphyrin, and 5,15-dimesityl-10-[3,5-bis{2-[4-(N,N’-difluoroboryl-1,9-dimethyidipyrrin-5-yl)-phenyl]ethynyl}phenyl]-20-(4-iodophenyl)porphyrin.Computed Properties of C7H5IO
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com