Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone O-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization and Oxidation

Shunsuke Chiba; Mitsuru Kitamura; Osamu Saku; Koichi Narasaka

doi:10.1246/bcsj.77.785

Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone O-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization and Oxidation

Shunsuke Chiba, Mitsuru Kitamura, Osamu Saku, Koichi Narasaka^*

^*Corresponding author for this work

The University of Tokyo

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

61 Citations (Scopus)

Abstract

Various 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by treatment with a catalytic amount of Pd(dba) ₂-t-Bu₃P (dba = dibenzylideneacetone) and triethylamine in the presence of MS 4A via alkylideneaminopalladium(II) intermediates generated by oxidative addition of the oximes to a Pd(0) complex.

Original language	English
Pages (from-to)	785-796
Number of pages	12
Journal	Bulletin of the Chemical Society of Japan
Volume	77
Issue number	4
DOIs	https://doi.org/10.1246/bcsj.77.785
Publication status	Published - 2004
Externally published	Yes

ASJC Scopus Subject Areas

General Chemistry

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title = "Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone O-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization and Oxidation",

abstract = "Various 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by treatment with a catalytic amount of Pd(dba) 2-t-Bu3P (dba = dibenzylideneacetone) and triethylamine in the presence of MS 4A via alkylideneaminopalladium(II) intermediates generated by oxidative addition of the oximes to a Pd(0) complex.",

author = "Shunsuke Chiba and Mitsuru Kitamura and Osamu Saku and Koichi Narasaka",

year = "2004",

doi = "10.1246/bcsj.77.785",

language = "English",

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pages = "785--796",

journal = "Bulletin of the Chemical Society of Japan",

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T1 - Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone O-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization and Oxidation

AU - Chiba, Shunsuke

AU - Kitamura, Mitsuru

AU - Saku, Osamu

AU - Narasaka, Koichi

PY - 2004

Y1 - 2004

N2 - Various 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by treatment with a catalytic amount of Pd(dba) 2-t-Bu3P (dba = dibenzylideneacetone) and triethylamine in the presence of MS 4A via alkylideneaminopalladium(II) intermediates generated by oxidative addition of the oximes to a Pd(0) complex.

AB - Various 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by treatment with a catalytic amount of Pd(dba) 2-t-Bu3P (dba = dibenzylideneacetone) and triethylamine in the presence of MS 4A via alkylideneaminopalladium(II) intermediates generated by oxidative addition of the oximes to a Pd(0) complex.

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DO - 10.1246/bcsj.77.785

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JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

IS - 4

ER -

Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone O-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization and Oxidation

Abstract

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