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Ferrocenylindium Reagents in Palladium‐Catalyzed Cross‐Coupling Reactions: Asymmetric Synthesis of Planar Chiral 2‐Aryl Oxazolyl and Sulfinyl Ferrocenes
Author(s) -
Mato Mauro,
PérezCaaveiro Cristina,
Sarandeses Luis A.,
Pérez Sestelo José
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601397
Subject(s) - transmetalation , chemistry , palladium , aryl , electrophile , reagent , catalysis , combinatorial chemistry , coupling reaction , stereoselectivity , enantioselective synthesis , medicinal chemistry , organic synthesis , organic chemistry , alkyl
The preparation of ferrocenylindium species and palladium‐catalyzed cross‐coupling reactions for the synthesis of monosubstituted and planar chiral 1,2‐disubstituted ferrocenes is described. Triferrocenylindium reagents (Fc 3 In) are efficiently prepared in a one‐pot procedure from ferrocenes by lithiation and transmetallation to indium using InCl 3 . The palladium‐catalyzed cross‐coupling reactions of Fc 3 In (40 mol%) with a variety of organic electrophiles (aryl, heteroaryl, benzyl, alkenyl and acyl halides) in THF at 80 °C overnight provided a wide variety of monosubstituted ferrocenes in good to excellent yields. This methodology allowed the stereoselective synthesis of planar chiral 2‐aryl‐1‐oxazolylferrocenes and 2‐aryl‐1‐sulfinylferrocenes, which are of interest in asymmetric catalysis.