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Palladium‐Catalyzed Carbonylative Synthesis of 2,3‐Disubstituted Chromones
Author(s) -
Shen Chaoren,
Li Wanfang,
Yin Hongfei,
Spannenberg Anke,
Skrydstrup Troels,
Wu XiaoFeng
Publication year - 2016
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.201500858
Subject(s) - chemistry , carbonylation , palladium , intramolecular force , catalysis , ketone , claisen rearrangement , medicinal chemistry , nucleophile , organic chemistry , carbon monoxide
An unexpected palladium‐catalyzed carbonylative synthesis of 2,3‐disubstituted chromones has been developed. Starting from 2‐bromofluorobenzenes and ketones, the corresponding chromones were produced in good yields. By control experiments, this transformation was found to proceed through a sequential carbonylation/Claisen–Hasse rearrangement/intramolecular nucleophilic aromatic substitution approach (S N Ar). More specifically, the reaction sequence started with a palladium‐catalyzed carbonylation of the ketone with o ‐bromofluorobenzene to give the vinyl benzoates, which subsequently transformed into 1,3‐diketones via a Claisen–Hasse rearrangement. The final products were produced after an intramolecular S N Ar reaction of the in situ formed 1,3‐diketone.