Premium
A Deacetylation–Diazotation–Coupling Sequence: Palladium‐ Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups
Author(s) -
Schmidt Bernd,
Berger René
Publication year - 2013
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.201200929
Subject(s) - chemistry , acetanilide , catalysis , palladium , sequence (biology) , reagent , combinatorial chemistry , cycloaddition , coupling reaction , polymer chemistry , organic chemistry , photochemistry , biochemistry
Acetanilides can be deacetylated and diazotized in situ , and subsequently used in Pd‐catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki cross‐coupling reactions, and a Pd‐catalyzed [2+2+1] cycloaddition have been investigated as terminating CC bond‐forming steps of this one‐flask sequence. The sequence does not require the exchange of solvents or removal of by‐products between the individual steps, but proceeds by addition of reagents and catalysts in due course.