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Expeditious Synthesis of Functionalized 1‐Arylcyclooctadienes via Palladium‐Catalyzed Lithium Cross‐Coupling
Author(s) -
Wandler Angela E. E.,
Bräse Stefan
Publication year - 2016
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.201600887
Subject(s) - chemistry , palladium , catalysis , lithium (medication) , aryl , selectivity , halogen , coupling reaction , coupling (piping) , combinatorial chemistry , organic chemistry , metallurgy , medicine , alkyl , endocrinology , materials science
The palladium‐catalyzed direct cross‐coupling of aryl bromides and (1 Z ,5 Z )‐cycloocta‐1,5‐dien‐1‐yllithium is described as an important method to synthesize 1‐arylcyclooctadienes. The use of a well‐established Pd 2 dba 3 /XPhos catalytic system affords the desired new compounds in good to excellent yields; the reaction proceeds at room temperature with both high efficiency and selectivity. Finally we found the best conditions to combine a suitable lithium‐halogen exchange with a cross‐coupling reaction.