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Continuous Flow Synthesis of Ketones from Carbon Dioxide and Organolithium or Grignard Reagents
Author(s) -
Wu Jie,
Yang Xiaoqing,
He Zhi,
Mao Xianwen,
Hatton T. Alan,
Jamison Timothy F.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201405014
Subject(s) - reagent , ketone , solvent , continuous flow , flow chemistry , chemistry , reactivity (psychology) , alcohol , organic chemistry , carbon dioxide , combinatorial chemistry , materials science , catalysis , medicine , alternative medicine , pathology , physics , mechanics
We describe an efficient continuous flow synthesis of ketones from CO 2 and organolithium or Grignard reagents that exhibits significant advantages over conventional batch conditions in suppressing undesired symmetric ketone and tertiary alcohol byproducts. We observed an unprecedented solvent‐dependence of the organolithium reactivity, the key factor in governing selectivity during the flow process. A facile, telescoped three‐step–one‐flow process for the preparation of ketones in a modular fashion through the in‐line generation of organometallic reagents is also established.