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

Funding

We thank MEXT for financial support KAKENHI (15H05754 for E.N. and Grant-in-Aid for Scientific Research on Innovative Areas No. 16H01005 to L.I.). Y.A. gratefully acknowledges financial support from the Scientific and Technological Research Council of Turkey (TUBİTAK) through the BIDEB-2219 Postdoctoral Research Fellowship Program (Project No. 1059B191500481) and Istanbul Technical University Scientific Research Foundation (BAP Project No. 39043). T.M. thanks the Japan Society for the Promotion of Science for Young Scientists for research fellowship No. 26–11422.

Funders	Funder number
Istanbul Technical University Scientific Research Foundation
British Association for Psychopharmacology	39043
Japan Society for the Promotion of Science	26–11422
Ministry of Education, Culture, Sports, Science and Technology	15H05754, 16H01005
Türkiye Bilimsel ve Teknolojik Araştırma Kurumu	1059B191500481

Keywords

C−H activation
alkynes
amides
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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language = "English",

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AU - Matsubara, Tatsuaki

AU - Nakamura, Eiichi

PY - 2018/7

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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 - C−H activation

KW - alkynes

KW - amides

KW - indenones

KW - iron

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ER -

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

Abstract

Bibliographical note

Funding

Keywords

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