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Reissert‐Type Acylation with Acylzirconocene Chloride Complexes
Author(s) -
Saito Akio,
Sakurai Hikaru,
Sudo Kohei,
Murai Kosuke,
Hanzawa Yuji
Publication year - 2013
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.201301264
Subject(s) - chemistry , acylation , regioselectivity , isoquinoline , adduct , cationic polymerization , catalysis , medicinal chemistry , chloride , organic chemistry , solvent
In the presence of ClCO 2 Et, the use of CuI in MeNO 2 efficiently catalyzed the Reissert‐type acylation of isoquinoline derivatives with acylzirconocene chlorides. In the reaction of quinolines with acylzirconocene chlorides, the choice of catalyst and solvent was crucial to the regioselective formation of adducts. The cationic Rh I ‐catalyzed reaction in MeNO 2 preferentially afforded 1,2 adducts. On the other hand, the Cu I ‐catalyzed reaction in CH 2 Cl 2 preferentially afforded 1,4 adducts.