Dehydrogenative Cycloisomerization/Arylation Sequence of N-Propargyl Carboxamides with Arenes by Iodine(III)-Catalysis

Yuki Umakoshi; Yusuke Takemoto; Akira Tsubouchi; Viktor V. Zhdankin; Akira Yoshimura; Akio Saito

doi:10.1002/adsc.202200219

Dehydrogenative Cycloisomerization/Arylation Sequence of N-Propargyl Carboxamides with Arenes by Iodine(III)-Catalysis

Yuki Umakoshi, Yusuke Takemoto, Akira Tsubouchi, Viktor V. Zhdankin, Akira Yoshimura, Akio Saito

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

6 Scopus citations

Abstract

Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile-tethered unactivated alkynes provides a facile and powerful approach to C−C bond formation between the generated heterocycles and unfunctionalized arenes. Here, we describe a hypervalent iodine(III)-catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from N-propargyl carboxamides and arenes, representing first C(sp³)−C(sp²) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in exo-dig modes. (Figure presented.).

Original language	English (US)
Pages (from-to)	2053-2059
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	12
DOIs	https://doi.org/10.1002/adsc.202200219
State	Published - Jun 21 2022
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported partly by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JPMJCR19R2). V.V.Z. and A.Y. are thankful to National Science Foundation (CHE‐1759798).

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

arylation
catalysis
cyclization
iodine
metal-free

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title = "Dehydrogenative Cycloisomerization/Arylation Sequence of N-Propargyl Carboxamides with Arenes by Iodine(III)-Catalysis",

abstract = "Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile-tethered unactivated alkynes provides a facile and powerful approach to C−C bond formation between the generated heterocycles and unfunctionalized arenes. Here, we describe a hypervalent iodine(III)-catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from N-propargyl carboxamides and arenes, representing first C(sp3)−C(sp2) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in exo-dig modes. (Figure presented.).",

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author = "Yuki Umakoshi and Yusuke Takemoto and Akira Tsubouchi and Zhdankin, {Viktor V.} and Akira Yoshimura and Akio Saito",

note = "Funding Information: This work was supported partly by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JPMJCR19R2). V.V.Z. and A.Y. are thankful to National Science Foundation (CHE‐1759798). Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

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AU - Umakoshi, Yuki

AU - Takemoto, Yusuke

AU - Tsubouchi, Akira

AU - Zhdankin, Viktor V.

AU - Yoshimura, Akira

AU - Saito, Akio

N1 - Funding Information: This work was supported partly by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JPMJCR19R2). V.V.Z. and A.Y. are thankful to National Science Foundation (CHE‐1759798). Publisher Copyright: © 2022 Wiley-VCH GmbH.

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N2 - Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile-tethered unactivated alkynes provides a facile and powerful approach to C−C bond formation between the generated heterocycles and unfunctionalized arenes. Here, we describe a hypervalent iodine(III)-catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from N-propargyl carboxamides and arenes, representing first C(sp3)−C(sp2) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in exo-dig modes. (Figure presented.).

AB - Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile-tethered unactivated alkynes provides a facile and powerful approach to C−C bond formation between the generated heterocycles and unfunctionalized arenes. Here, we describe a hypervalent iodine(III)-catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from N-propargyl carboxamides and arenes, representing first C(sp3)−C(sp2) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in exo-dig modes. (Figure presented.).

KW - arylation

KW - catalysis

KW - cyclization

KW - iodine

KW - metal-free

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Dehydrogenative Cycloisomerization/Arylation Sequence of N-Propargyl Carboxamides with Arenes by Iodine(III)-Catalysis

Abstract

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Keywords

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