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A 1,3‐Lithium Shift of Propargylic/Allenylic Lithium and the Subsequent Transmetalation Coupling Reaction with Aryl Halides
Author(s) -
Ma Shengming,
He Qiwen
Publication year - 2004
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.200352924
Subject(s) - transmetalation , lithium (medication) , halide , aryl , chemistry , coupling (piping) , inorganic chemistry , materials science , organic chemistry , catalysis , metallurgy , psychology , alkyl , psychiatry
The lithiation reagent and temperature may be the key factors controlling the 1,3‐lithium shift of propargylic/allenylic lithium (see scheme). Under the right conditions, 1,1‐diarylallenes and 1,3‐diarylallenes can be easily and highly selectively synthesized by the lithiation of 1‐aryl‐1‐alkynes and the subsequent transmetalation (1), and Pd‐catalyzed coupling with aryl halides (2).