Rhodium-Catalyzed β-Acylalkylation of Allylbenzene Derivatives with Allyl Alcohols via C-C Bond Cleavage

Soya Ishikawa; Ryo Togashi; Ryosuke Ueda; Shunsuke Onodera; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/acs.joc.2c02776

Rhodium-Catalyzed β-Acylalkylation of Allylbenzene Derivatives with Allyl Alcohols via C-C Bond Cleavage

Soya Ishikawa, Ryo Togashi, Ryosuke Ueda, Shunsuke Onodera, Takuya Kochi, Fumitoshi Kakiuchi

Department of Chemistry

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

Abstract

We report here a deallylative β-acylalkylation reaction of allylbenzene derivatives with allyl alcohols in the presence of Cp*Rh catalysts. Allylbenzenes possessing pyridyl and pyrazolyl directing groups were converted to β-aryl ketones via the cleavage of C(aryl)-C(allyl) bonds. Synthesis of a quinoline derivative from a β-aryl ketone product bearing a pyrazolyl group was also achieved.

Original language	English
Pages (from-to)	3313-3320
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	88
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.2c02776
Publication status	Published - 2023 Mar 3

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.2c02776

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title = "Rhodium-Catalyzed β-Acylalkylation of Allylbenzene Derivatives with Allyl Alcohols via C-C Bond Cleavage",

abstract = "We report here a deallylative β-acylalkylation reaction of allylbenzene derivatives with allyl alcohols in the presence of Cp*Rh catalysts. Allylbenzenes possessing pyridyl and pyrazolyl directing groups were converted to β-aryl ketones via the cleavage of C(aryl)-C(allyl) bonds. Synthesis of a quinoline derivative from a β-aryl ketone product bearing a pyrazolyl group was also achieved.",

author = "Soya Ishikawa and Ryo Togashi and Ryosuke Ueda and Shunsuke Onodera and Takuya Kochi and Fumitoshi Kakiuchi",

note = "Funding Information: F.K. is thankful for financial support, in part, from the Japanese Society for the Promotion of Science (JSPS) Grant-in-Aid for Scientific Research 21H01944, Japan, and JST CREST Grant No. JPMJSP2123. Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

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doi = "10.1021/acs.joc.2c02776",

language = "English",

volume = "88",

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journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Rhodium-Catalyzed β-Acylalkylation of Allylbenzene Derivatives with Allyl Alcohols via C-C Bond Cleavage

AU - Ishikawa, Soya

AU - Togashi, Ryo

AU - Ueda, Ryosuke

AU - Onodera, Shunsuke

AU - Kochi, Takuya

AU - Kakiuchi, Fumitoshi

N1 - Funding Information: F.K. is thankful for financial support, in part, from the Japanese Society for the Promotion of Science (JSPS) Grant-in-Aid for Scientific Research 21H01944, Japan, and JST CREST Grant No. JPMJSP2123. Publisher Copyright: © 2023 American Chemical Society.

PY - 2023/3/3

Y1 - 2023/3/3

N2 - We report here a deallylative β-acylalkylation reaction of allylbenzene derivatives with allyl alcohols in the presence of Cp*Rh catalysts. Allylbenzenes possessing pyridyl and pyrazolyl directing groups were converted to β-aryl ketones via the cleavage of C(aryl)-C(allyl) bonds. Synthesis of a quinoline derivative from a β-aryl ketone product bearing a pyrazolyl group was also achieved.

AB - We report here a deallylative β-acylalkylation reaction of allylbenzene derivatives with allyl alcohols in the presence of Cp*Rh catalysts. Allylbenzenes possessing pyridyl and pyrazolyl directing groups were converted to β-aryl ketones via the cleavage of C(aryl)-C(allyl) bonds. Synthesis of a quinoline derivative from a β-aryl ketone product bearing a pyrazolyl group was also achieved.

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U2 - 10.1021/acs.joc.2c02776

DO - 10.1021/acs.joc.2c02776

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Rhodium-Catalyzed β-Acylalkylation of Allylbenzene Derivatives with Allyl Alcohols via C-C Bond Cleavage

Abstract

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