Harnessing [1,4], [1,5], and [1,6] Anionic Fries-type Rearrangements by Reaction-Time Control in Flow

Angewandte Chemie
Heejin KimJun-Ichi Yoshida

Abstract

A series of anionic Fries-type rearrangements of carbamoyl-substituted aryllithium intermediates were controlled by using flow microreactor systems. For the [1,4] and [1,5] rearrangements, the aryllithium intermediate formed before carbamoyl migration and the lithium alkoxide formed after carbamoyl migration can be selectively subjected to subsequent reactions with electrophiles by precisely controlling the residence time and temperature (-25 to -50 °C). In contrast, the [1,6] rearrangement is rather slow even at -25 °C. The absence of crossover products indicates the intramolecular nature of the carbamoyl group migration.

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Citations

Feb 10, 2018·Angewandte Chemie·Heejin KimJun-Ichi Yoshida
May 9, 2019·Chemical Society Reviews·Marcus Korb, Heinrich Lang
Apr 5, 2018·Organic Letters·Claudia FebereroRoberto Sanz
Sep 9, 2020·The Journal of Organic Chemistry·Claudia FebereroRoberto Sanz

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