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Efficient Pd‐Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents
Author(s) -
Scherpf Thorsten,
Steinert Henning,
Großjohann Angela,
Dilchert Katharina,
Tappen Jens,
Rodstein Ilja,
Gessner Viktoria H.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202008866
Subject(s) - transmetalation , aryl , reagent , chemistry , palladium , combinatorial chemistry , catalysis , coupling reaction , organic chemistry , alkyl
Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C−C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been achieved, Csp 2 −Csp 3 coupling reactions are very limited. Herein, we report the first general protocol for the coupling or aryl chlorides with alkyllithium reagents. Palladium catalysts based on ylide‐substituted phosphines (YPhos) were found to be excellently suited for this transformation giving high selectivities at room temperature with a variety of aryl chlorides without the need for an additional transmetallation reagent. This is demonstrated in gram‐scale synthesis including building blocks for materials chemistry and pharmaceutical industry. Furthermore, the direct coupling of aryllithiums as well as Grignard reagents with aryl chlorides was also easily accomplished at room temperature.