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

^*Bu çalışma için yazışmadan sorumlu yazar

Temel Bilimler Bölümü

The University of Tokyo
RIKEN

Araştırma sonucu: Dergiye katkı › Makale › bilirkişi

28 Atıf (Scopus)

Özet

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.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	1327-1329
Sayfa sayısı	3
Dergi	Asian Journal of Organic Chemistry
Hacim	7
Basın numarası	7
DOI'lar	https://doi.org/10.1002/ajoc.201800200
Yayın durumu	Yayınlandı - Tem 2018

Bibliyografik not

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

Finansman

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.

Finansörler	Finansör numarası
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

Belgeye Erişim

10.1002/ajoc.201800200

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

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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.",

keywords = "C−H activation, alkynes, amides, indenones, iron",

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

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = jul,

doi = "10.1002/ajoc.201800200",

language = "English",

volume = "7",

pages = "1327--1329",

journal = "Asian Journal of Organic Chemistry",

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TY - JOUR

T1 - Iron-Catalyzed Synthesis of Indenones through Cyclization of Carboxamides with Alkynes

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 - C−H activation

KW - alkynes

KW - amides

KW - indenones

KW - iron

UR - https://www.scopus.com/pages/publications/85046664608

U2 - 10.1002/ajoc.201800200

DO - 10.1002/ajoc.201800200

M3 - Article

AN - SCOPUS:85046664608

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

Özet

Bibliyografik not

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

Parmak izi

Alıntı Yap