Pummerer Synthesis of Chromanes Reveals a Competition
between Cyclization and Reductive Chlorination
Posted on 2019-08-23 - 12:08
The competition between
an unprecedented reductive chlorination
and the Pummerer reaction was studied and applied to the synthesis
of benzofused oxygen heterocycles including 3-aminochromanes and in
the intramolecular chlorination of activated aromatic rings. The use
of (COCl)2 as a Pummerer activator showed substantial activity,
producing α-chlorinated sulfides that can undergo Pummerer–Friedel–Crafts
cyclization. If the aromatic ring has electron-donating groups in
position three, then the reaction follows a different pathway, yielding
the reductive chlorination products, where the chlorine atom comes
from a sulfonium salt.
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Acosta-Guzmán, Paola; Rodríguez-López, Alvaro; Gamba-Sánchez, Diego (2019). Pummerer Synthesis of Chromanes Reveals a Competition
between Cyclization and Reductive Chlorination. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b02520
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AUTHORS (3)
PA
Paola Acosta-Guzmán
AR
Alvaro Rodríguez-López
DG
Diego Gamba-Sánchez