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Mizoroki–Heck Reactions with 4‐Phenoldiazonium Salts
Author(s) -
Schmidt Bernd,
Hölter Frank,
Berger René,
Jessel Sönke
Publication year - 2010
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.201000493
Subject(s) - chemistry , acetanilide , salt (chemistry) , sequence (biology) , catalysis , combinatorial chemistry , palladium , alkylation , organic chemistry , biochemistry
Significantly better yields were achieved in Mizoroki–Heck reactions using 4‐phenoldiazonium salts instead of their O ‐alkylated analogues under otherwise identical conditions. We found that a one‐flask deacetylation–diazotation–precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these arylating agents in palladium‐catalyzed CC bond forming reactions was demonstrated for a one‐flask‐synthesis of the heterocyclic core of the drug aripiprazole. Notably, the diazonium salt formation from an acetanilide could be combined with two Pd‐catalyzed steps in a one‐flask sequence, without any exchange of solvents or isolation of intermediates.