Phosphazene Base tBu-P4 Catalyzed Methoxy–Alkoxy Exchange Reaction on (Hetero)Arenes

Masanori Shigeno; Kazutoshi Hayashi; Kanako Nozawa-Kumada; Yoshinori Kondo

doi:10.1002/chem.201900498

Phosphazene Base tBu-P4 Catalyzed Methoxy–Alkoxy Exchange Reaction on (Hetero)Arenes

Masanori Shigeno, Kazutoshi Hayashi, Kanako Nozawa-Kumada, Yoshinori Kondo

PHA - Molecular Pharmaceutical Science

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

12 Citations (Scopus)

Abstract

The organic superbase tBu-P4 catalyzes methoxy-alkoxy exchange reactions on (hetero)arenes with alcohols. The catalytic reaction proceeded efficiently with electron-deficient methoxy(hetero)arenes as well as with a variety of alcohols, including 3-amino-1-propanol, β-citronellol, menthol, and cholesterol. An intramolecular version of this reaction furnished six- and seven-membered ring compounds.

Original language	English
Pages (from-to)	6077-6081
Number of pages	5
Journal	Chemistry - A European Journal
Volume	25
Issue number	24
DOIs	https://doi.org/10.1002/chem.201900498
Publication status	Published - 2019 Apr 26

Keywords

alcohols
aromatic substitution
methoxyarenes
organocatalysis
phosphazenes

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Phosphazene Base tBu-P4 Catalyzed Methoxy–Alkoxy Exchange Reaction on (Hetero)Arenes",

abstract = "The organic superbase tBu-P4 catalyzes methoxy-alkoxy exchange reactions on (hetero)arenes with alcohols. The catalytic reaction proceeded efficiently with electron-deficient methoxy(hetero)arenes as well as with a variety of alcohols, including 3-amino-1-propanol, β-citronellol, menthol, and cholesterol. An intramolecular version of this reaction furnished six- and seven-membered ring compounds.",

keywords = "alcohols, aromatic substitution, methoxyarenes, organocatalysis, phosphazenes",

author = "Masanori Shigeno and Kazutoshi Hayashi and Kanako Nozawa-Kumada and Yoshinori Kondo",

year = "2019",

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T1 - Phosphazene Base tBu-P4 Catalyzed Methoxy–Alkoxy Exchange Reaction on (Hetero)Arenes

AU - Shigeno, Masanori

AU - Hayashi, Kazutoshi

AU - Nozawa-Kumada, Kanako

AU - Kondo, Yoshinori

PY - 2019/4/26

Y1 - 2019/4/26

N2 - The organic superbase tBu-P4 catalyzes methoxy-alkoxy exchange reactions on (hetero)arenes with alcohols. The catalytic reaction proceeded efficiently with electron-deficient methoxy(hetero)arenes as well as with a variety of alcohols, including 3-amino-1-propanol, β-citronellol, menthol, and cholesterol. An intramolecular version of this reaction furnished six- and seven-membered ring compounds.

AB - The organic superbase tBu-P4 catalyzes methoxy-alkoxy exchange reactions on (hetero)arenes with alcohols. The catalytic reaction proceeded efficiently with electron-deficient methoxy(hetero)arenes as well as with a variety of alcohols, including 3-amino-1-propanol, β-citronellol, menthol, and cholesterol. An intramolecular version of this reaction furnished six- and seven-membered ring compounds.

KW - alcohols

KW - aromatic substitution

KW - methoxyarenes

KW - organocatalysis

KW - phosphazenes

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