86863-92-5Relevant academic research and scientific papers
A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups
Nagaki, Aiichiro,Kim, Heejin,Moriwaki, Yuya,Matsuo, Chika,Yoshida, Jun-Ichi
supporting information; experimental part, p. 11167 - 11177 (2010/11/04)
A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para-, meta-, and ortho-positions. Alkyl p- and m-lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o-lithiobenzoates were successfully generated by the Br/ Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.
Aryllithium compounds bearing alkoxycarbonyl groups: Generation and reactions using a microflow system
Nagaki, Aiichiro,Kim, Heejin,Yoshida, Jun-Ichi
supporting information; experimental part, p. 7833 - 7836 (2009/04/10)
Go with the flow: An effective method for the generation and reaction of aryllithium compounds bearing an alkoxycarbonyl group is developed using microflow systems with very short residence times together with fast mixing and efficient temperature control. A wide range of alkoxycarbonyl groups including ethoxycarbonyl and methoxycarbonyl groups are tolerant of the microflow conditions. (Chemical Equation Presented)
