Palladium-Catalyzed Carbonylative Synthesis of 2,3-Disubstituted Chromones

Chaoren Shen; Wanfang Li; Hongfei Yin; Anke Spannenberg; Troels Skrydstrup; Xiao-Feng Wu

doi:10.1002/adsc.201500858

Palladium-Catalyzed Carbonylative Synthesis of 2,3-Disubstituted Chromones

Chaoren Shen, Wanfang Li, Hongfei Yin, Anke Spannenberg, Troels Skrydstrup, Xiao-Feng Wu

Interdisciplinary Nanoscience Center - INANO-Kemi, iNANO-huset

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

35 Citations (Scopus)

Abstract

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 _NAr). 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 _NAr reaction of the in situ formed 1,3-diketone.

Original language	English
Journal	Advanced Synthesis & Catalysis
Volume	358
Issue	3
Pages (from-to)	466-479
Number of pages	14
ISSN	1615-4150
DOIs	https://doi.org/10.1002/adsc.201500858
Publication status	Published - 4 Feb 2016

Keywords

Claisen-Hasse rearrangement
carbonylation
chromones
nucleophilic aromatic substitution
palladium catalysts

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10.1002/adsc.201500858

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title = "Palladium-Catalyzed Carbonylative Synthesis of 2,3-Disubstituted Chromones",

abstract = "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 NAr). 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 NAr reaction of the in situ formed 1,3-diketone.",

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AU - Li, Wanfang

AU - Yin, Hongfei

AU - Spannenberg, Anke

AU - Skrydstrup, Troels

AU - Wu, Xiao-Feng

PY - 2016/2/4

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AB - 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 NAr). 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 NAr reaction of the in situ formed 1,3-diketone.

KW - Claisen-Hasse rearrangement

KW - carbonylation

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KW - nucleophilic aromatic substitution

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Palladium-Catalyzed Carbonylative Synthesis of 2,3-Disubstituted Chromones

Abstract

Keywords

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