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Application of a Ferrocene‐Based Palladacycle Precatalyst to Enantioselective Aryl‐Aryl Kumada Coupling
Author(s) -
Arthurs Ross A.,
Hughes David L.,
Richards Christopher J.
Publication year - 2022
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202101077
Subject(s) - chemistry , diphenylphosphine , palladium , aryl , denticity , ligand (biochemistry) , ferrocene , medicinal chemistry , bromide , coupling reaction , enantioselective synthesis , organopalladium , catalysis , organic chemistry , crystal structure , phosphine , alkyl , biochemistry , receptor , electrode , electrochemistry
The palladium catalysed reaction of 1‐iodo‐2‐methylnaphthalene and 2‐methyl‐1‐naphthylmagnesium bromide gave quantitatively an ( S a )‐configured cross‐coupled product in 80 % e.e. using ( R , S p )‐PPFA as a ligand. N , N ‐Dimethylaminomethylferrocene was cyclopalladated (Na 2 PdCl 4 , ( S )−Ac−Phe−OH, 93 % e.e., as determined by 1 H NMR as a result of self‐induced non‐equivalence), and the resulting ( S p )‐configured dimeric palladacycle was employed as a precatalyst for this cross‐coupling reaction (5 mol%). Addition to the palladacycle of diphenylphosphine and subsequent base‐promoted bidentate ligand synthesis and palladium capture gave an in situ generated catalyst resulting in an ( S p )‐configured product in up to 71 % e.e.
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