Flow on: Flow microreactors enable the generation of aryl lithium compounds and subsequent electrophilic fluorination with NFSI and N‐fluorosultam. The reaction can be successfully accomplished to synthesize various aryl fluorides involving an electron‐withdrawing, an electron‐donating, and a sterically hindered functional group in good yields.
Pauson-Khand reactions were achieved at ambient temperature without any additive using a photochemical flow microreactor. The efficiency of the reaction was better than that in a conventional batch reactor, and the reaction could be operated continuously for 1 h.
SummaryThe use of FeCl3 resulted in a fast homocoupling of aryllithiums, and this enabled its integration with the halogen–lithium exchange reaction of aryl halides in a flow microreactor. This system allows the homocoupling of two aryl halides bearing electrophilic functional groups, such as CN and NO2, in under a minute.
Condensation of carboxylic acids 1 and 5 with unprotected α-amino acids 2 via activation by ethyl chloroformate and triethylamine proceeded effectively to afford the corresponding amides in 50–99% yields. Tripeptide 7c was obtained in 42% yield from the dipeptide 6c in a similar manner.
New methods for the synthesis of functionalized aryl fluorides (II) (18 examples) based on organo-lithium chemistry in flow microreactors and use of electrophilic fluorinating reagents are developed. -(NAGAKI, A.; UESUGI, Y.; KIM, H.; YOSHIDA*, J.-I.; Chem. -Asian J. 8 (2013) 4, 705-708, http://dx.doi.org/10.1002/asia.201201191 ; Dep. Synth. Chem. Biol. Chem., Grad. Sch. Eng., Kyoto Univ., Nishikyo, Kyoto 615, Japan; Eng.) -R. Staver 34-052
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