Palladium-Catalyzed C8-Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton

Caroline Berrou; Sébastien Prévost

doi:10.1002/adsc.202100317

Palladium-Catalyzed C8-Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton

Caroline Berrou
, Sébastien Prévost

Laboratoire de Synthèse Organique

Research output: Contribution to journal › Article › peer-review

Abstract

Herein, a direct C8-oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium-catalyzed oxidation reaction using PhI(OAc)₂ in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to the synthesis of variously substituted naphtholactones. (Figure presented.).

Original language	English
Pages (from-to)	4091-4095
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	16
DOIs	https://doi.org/10.1002/adsc.202100317
Publication status	Published - 13 Aug 2021
Externally published	Yes

Keywords

1-carbonylnaphthalene
C−H oxygenation
naphtholactone
oxidation
palladium catalysis

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10.1002/adsc.202100317

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title = "Palladium-Catalyzed C8-Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton",

abstract = "Herein, a direct C8-oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium-catalyzed oxidation reaction using PhI(OAc)2 in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to the synthesis of variously substituted naphtholactones. (Figure presented.).",

keywords = "1-carbonylnaphthalene, C−H oxygenation, naphtholactone, oxidation, palladium catalysis",

author = "Caroline Berrou and S{\'e}bastien Pr{\'e}vost",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH.",

year = "2021",

month = aug,

day = "13",

doi = "10.1002/adsc.202100317",

language = "English",

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journal = "Advanced Synthesis and Catalysis",

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T1 - Palladium-Catalyzed C8-Oxygenation of Naphthalene Derivatives

T2 - Direct Access to Naphtholactone Skeleton

AU - Berrou, Caroline

AU - Prévost, Sébastien

PY - 2021/8/13

Y1 - 2021/8/13

N2 - Herein, a direct C8-oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium-catalyzed oxidation reaction using PhI(OAc)2 in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to the synthesis of variously substituted naphtholactones. (Figure presented.).

AB - Herein, a direct C8-oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium-catalyzed oxidation reaction using PhI(OAc)2 in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to the synthesis of variously substituted naphtholactones. (Figure presented.).

KW - 1-carbonylnaphthalene

KW - C−H oxygenation

KW - naphtholactone

KW - oxidation

KW - palladium catalysis

U2 - 10.1002/adsc.202100317

DO - 10.1002/adsc.202100317

M3 - Article

AN - SCOPUS:85109911293

SN - 1615-4150

VL - 363

SP - 4091

EP - 4095

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 16

ER -

Palladium-Catalyzed C8-Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton

Abstract

Keywords

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