Premium
Improved Air‐Stable Solid Aromatic and Heterocyclic Zinc Reagents by Highly Selective Metalations for Negishi Cross‐Couplings
Author(s) -
Stathakis Christos I.,
Bernhardt Sebastian,
Quint Valentin,
Knochel Paul
Publication year - 2012
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.201204526
Subject(s) - transmetalation , negishi coupling , zinc , metalation , aryl , chemistry , reagent , solvent , yield (engineering) , evaporation , combinatorial chemistry , organic chemistry , materials science , physics , catalysis , alkyl , metallurgy , thermodynamics
Directed metalation using TMPMgCl ⋅ LiCl (TMP=2,2,6,6‐tetramethylpiperidide) and subsequent transmetalation with Zn(OPiv) 2 leads to aryl and heteroaryl zinc pivalates. After solvent evaporation, easy‐to‐handle fine powders are obtained that retain most of their activity (>85 %) when exposed to air for 4 h. They smoothly undergo Negishi cross‐couplings, and technical‐grade solvents can be used without significant loss of yield.