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Ligand Effect on Iron‐Catalyzed Cross‐Coupling Reactions: Evaluation of Amides as O‐Coordinating Ligands
Author(s) -
Bisz Elwira,
Kardela Marlena,
Szostak Michal
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201901150
Subject(s) - chemistry , catalysis , amide , ligand (biochemistry) , coupling reaction , reactivity (psychology) , steric effects , aryl , combinatorial chemistry , stereochemistry , organic chemistry , receptor , alternative medicine , pathology , medicine , biochemistry , alkyl
The development of new highly efficient O‐coordinating ligands for iron‐catalyzed C(sp 2 )−C(sp 3 ) cross‐coupling reactions is reported. A structure‐reactivity study on the effect of amides as ligands in the industrially‐important iron‐catalyzed cross‐coupling of aryl chlorides with challenging organometallics possessing β‐hydrogens was performed. Investigation of a series of new 21 ligands that rationally vary in O‐coordination aptitude as well as sterics around the amide bond pinpointed the features that are important for catalysis. The study led to the discovery of several highly efficient ligands for cross‐coupling, including TMU (TMU=tetramethylurea), N‐cyclic and coordinating benzamides. Crucially, the study demonstrates several avenues for replacing reprotoxic NMP, which is currently still the most common additive in industrial applications of sustainable iron‐catalyzed cross‐coupling chemistry.