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Updated: Sep 25, 2025

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Asymmetric Flow Reactions Catalyzed by Immobilized Diphenylprolinol Alkyl Ether: Michael Reaction and Domino
Yujiro Hayashi1, Shusuke Hattori1, Seitaro Koshino1
1Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki-Aza Aoba, Aoba-ku, Sendai, 980-8578, Japan.
Abstract:
Flow reactions using an immobilized diphenylprolinol alkyl ether catalyst 2 were investigated in three reactions of α,β-unsaturated aldehydes and nitroalkanes such as nitromethane 3, nitroethanol 10, and nitroalkane 11, bearing two carbonyl groups. Whereas reactions using the corresponding monomer catalyst diphenylprolinol silyl ether 1 were slow, fast reactions were found with the immobilized polymer catalyst 2 in a batch system, and the latter was then applied to a flow system. In the Michael reaction of nitromethane 3, the polymer catalyst showed high reactivity in the initial 30 h and then decreased gradually. Good overall yield (72%) and turnover number (TON, 495) were obtained for a 60 h flow reaction, and the enantioselectivity of the product was excellent throughout. The TONs of domino reactions of nitroethanol 10 and nitroalkane 11, with two carbonyl groups, were 48 and 81, respectively.
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