Iron-Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes

Laurean Ilies; Yasin Arslanoglu; Tatsuaki Matsubara; Eiichi Nakamura

doi:10.1002/ajoc.201800200

Iron-Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes

Laurean Ilies^*, Yasin Arslanoglu, Tatsuaki Matsubara, Eiichi Nakamura

^*Corresponding author for this work

Department of Basic Sciences

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

27 Citations (Scopus)

Abstract

The iron/diphosphine-catalyzed annulation of a carboxamide possessing a bidentate directing group with an internal alkyne proceeds in the presence of phenylzinc halide as a base at 40 °C to produce a variety of indenone derivatives. The reaction proceeds through iron-catalyzed C−H bond activation of the carboxamide, followed by insertion of the alkyne into the resulting iron intermediate, and cyclization accelerated by the presence of Lewis acidic Zn^II. The reaction of naphthalene and anthraceneamide yields π-conjugated indenone derivatives.

Original language	English
Pages (from-to)	1327-1329
Number of pages	3
Journal	Asian Journal of Organic Chemistry
Volume	7
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201800200
Publication status	Published - Jul 2018

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

alkynes
amides
C−H activation
indenones
iron

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10.1002/ajoc.201800200

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title = "Iron-Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes",

abstract = "The iron/diphosphine-catalyzed annulation of a carboxamide possessing a bidentate directing group with an internal alkyne proceeds in the presence of phenylzinc halide as a base at 40 °C to produce a variety of indenone derivatives. The reaction proceeds through iron-catalyzed C−H bond activation of the carboxamide, followed by insertion of the alkyne into the resulting iron intermediate, and cyclization accelerated by the presence of Lewis acidic ZnII. The reaction of naphthalene and anthraceneamide yields π-conjugated indenone derivatives.",

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author = "Laurean Ilies and Yasin Arslanoglu and Tatsuaki Matsubara and Eiichi Nakamura",

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AU - Ilies, Laurean

AU - Arslanoglu, Yasin

AU - Matsubara, Tatsuaki

AU - Nakamura, Eiichi

PY - 2018/7

Y1 - 2018/7

N2 - The iron/diphosphine-catalyzed annulation of a carboxamide possessing a bidentate directing group with an internal alkyne proceeds in the presence of phenylzinc halide as a base at 40 °C to produce a variety of indenone derivatives. The reaction proceeds through iron-catalyzed C−H bond activation of the carboxamide, followed by insertion of the alkyne into the resulting iron intermediate, and cyclization accelerated by the presence of Lewis acidic ZnII. The reaction of naphthalene and anthraceneamide yields π-conjugated indenone derivatives.

AB - The iron/diphosphine-catalyzed annulation of a carboxamide possessing a bidentate directing group with an internal alkyne proceeds in the presence of phenylzinc halide as a base at 40 °C to produce a variety of indenone derivatives. The reaction proceeds through iron-catalyzed C−H bond activation of the carboxamide, followed by insertion of the alkyne into the resulting iron intermediate, and cyclization accelerated by the presence of Lewis acidic ZnII. The reaction of naphthalene and anthraceneamide yields π-conjugated indenone derivatives.

KW - alkynes

KW - amides

KW - C−H activation

KW - indenones

KW - iron

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DO - 10.1002/ajoc.201800200

M3 - Article

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SN - 2193-5807

VL - 7

SP - 1327

EP - 1329

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 7

ER -

Iron-Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes

Abstract

Bibliographical note

Keywords

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