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A Comparative Ancillary Ligand Survey in Palladium‐Catalyzed C–O Cross‐Coupling of Primary and Secondary Aliphatic Alcohols
Author(s) -
Sawatzky Ryan S.,
Hargreaves Breanna K. V.,
Stradiotto Mark
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600198
Subject(s) - chemistry , catalysis , palladium , aryl , halide , ligand (biochemistry) , coupling reaction , reactivity (psychology) , combinatorial chemistry , primary (astronomy) , organic chemistry , medicinal chemistry , medicine , biochemistry , alkyl , receptor , alternative medicine , physics , pathology , astronomy
The utility of RockPhos, Ad‐BippyPhos, JosiPhos (CyPF‐ t Bu), and Mor‐DalPhos in palladium‐catalyzed C–O cross‐coupling reactions involving aliphatic alcohols and (hetero)aryl halides under analogous conditions was examined, both at room temperature and at elevated temperature (90 °C). In general, the RockPhos‐based catalyst system proved superior, especially at room temperature, but catalysts based on the other ligands examined also proved effective across a range of C–O cross‐couplings, in some cases providing better catalytic performance than RockPhos. New reactivity was established in terms of the scope of room temperature reactions. Proof‐of‐principle examples of such cross‐couplings involving aryl mesylates were also demonstrated.