10.1021/acs.joc.7b01355.s001
Alessandra Casnati
Alessandra
Casnati
Raimondo Maggi
Raimondo
Maggi
Giovanni Maestri
Giovanni
Maestri
Nicola Della Ca’
Nicola Della
Ca’
Elena Motti
Elena
Motti
Pd-Catalyzed/Iodide-Promoted
α‑Arylation
of Ketones for the Regioselective Synthesis of Isocoumarins
American Chemical Society
2017
Regioselective Synthesis
reaction mixture
iodide anions
intramolecular cyclization process
phosphine-free one-pot synthesis features
access
Arylation
variety
palladium-catalyzed α- arylation step
2- halobenzoates
methodology
Pd-Catalyzed
2- bromobenzoates
selectivitie
Isocoumarin
antifungal activity
group tolerance
Xyridin
Ketone
yield
ketone
isocoumarin
2017-07-20 18:11:49
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Pd-Catalyzed_Iodide-Promoted_Arylation_of_Ketones_for_the_Regioselective_Synthesis_of_Isocoumarins/5229622
A variety of isocoumarins
have been synthesized directly from 2-halobenzoates
and ketones through a palladium-catalyzed α-arylation step followed
by an intramolecular cyclization process. The addition of iodide anions
to the reaction mixture increased yields and selectivities especially
when 2-bromobenzoates were employed. This phosphine-free one-pot synthesis
features a high functional group tolerance and gives access to richly
decorated isocoumarins. This general methodology was successful in the total synthesis of Xyridin
A, an important natural product with antibacterial and antifungal
activity.