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Continuous Synthesis of Organozinc Halides Coupled to Negishi Reactions
Author(s) -
Alonso Nerea,
Miller L. Zane,
de M. Muñoz Juan,
Alcázar Jesus,
McQuade D. Tyler
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400243
Subject(s) - negishi coupling , chemistry , halide , zinc , coupling reaction , combinatorial chemistry , coupling (piping) , organic chemistry , catalysis , metallurgy , materials science
The Negishi cross‐coupling is a powerful CC bond forming reaction. The method is less commonly used relative to other cross‐coupling methods in part due to lack of availability of organozinc species. While organozinc species can be prepared, problems with reproducibility and handling of these sensitive species can complicate these reactions. Herein, we describe the continuous formation, using an activated packed‐bed of metallic zinc, and subsequent use of organozinc halides. We demonstrate that a single column of zinc can provide excellent yields of organozinc halides and that they can be used downstream in subsequent Negishi cross‐couplings. The preparation of the zinc column and the scope of the reaction are discussed.