(2‐Ethylhexyl)sodium: A Hexane‐Soluble Reagent for Br/Na‐Exchanges and Directed Metalations in Continuous Flow | Zendy

Harenberg Johannes H. | Zendy; Weidmann Niels | Zendy; Wiegand Alexander J. | Zendy; Hoefer Carla A. | Zendy; Annapureddy Rajasekar Reddy | Zendy; Knochel Paul | Zendy

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(2‐Ethylhexyl)sodium: A Hexane‐Soluble Reagent for Br/Na‐Exchanges and Directed Metalations in Continuous Flow

Author(s) -

Harenberg Johannes H.,

Weidmann Niels,

Wiegand Alexander J.,

Hoefer Carla A.,

Annapureddy Rajasekar Reddy,

Knochel Paul

Publication year - 2021

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.202103031

Subject(s) - chemistry , reagent , electrophile , hexane , sodium , alkyl , flow chemistry , heptane , organic chemistry , combinatorial chemistry , catalysis

We report the on‐demand generation of hexane‐soluble (2‐ethylhexyl)sodium ( 1 ) from 3‐(chloromethyl)heptane ( 2 ) using a sodium‐packed‐bed reactor under continuous flow conditions. Thus, the resulting solution of 1 is free of elemental sodium and therefore suited for a range of synthetic applications. This new procedure avoids the storage of an alkylsodium and limits the handling of metallic sodium to a minimum. (2‐Ethylhexyl)sodium ( 1 ) proved to be a very useful reagent and undergoes in‐line Br/Na‐exchanges as well as directed sodiations. The resulting arylsodium intermediates are subsequently trapped in batch with various electrophiles such as ketones, aldehydes, Weinreb‐amides, imines, allyl bromides, disulfides and alkyl iodides. A reaction scale‐up of the Br/Na‐exchange using an in‐line electrophile quench was also reported.

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