Ruthenium-Catalyzed Ortho C-H Arylation of Aromatic Nitriles with Arylboronates and Observation of Partial Para Arylation

Yuta Koseki, Kentaroh Kitazawa, Masashi Miyake, Takuya Kochi, Fumitoshi Kakiuchi

研究成果: Article

8 引用 (Scopus)

抄録

Ruthenium-catalyzed C-H arylation of aromatic nitriles with arylboronates is described. The use of RuH2(CO){P(4-MeC6H4)3}3 as a catalyst provided higher yields of the ortho arylation products than the conventional RuH2(CO)(PPh3)3 catalyst. The arylation takes place mostly at the ortho positions, but unprecedented para arylation was also partially observed to give ortho,para diarylation products. In addition to C-H bond cleavage, the cyano group was also found to function as a directing group for cleavage of C-O bonds in aryl ethers.

元の言語English
ページ(範囲)6503-6510
ページ数8
ジャーナルJournal of Organic Chemistry
82
発行部数13
DOI
出版物ステータスPublished - 2017 7 7

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Nitriles
Ruthenium
Catalysts
Ethers

ASJC Scopus subject areas

  • Organic Chemistry

これを引用

Ruthenium-Catalyzed Ortho C-H Arylation of Aromatic Nitriles with Arylboronates and Observation of Partial Para Arylation. / Koseki, Yuta; Kitazawa, Kentaroh; Miyake, Masashi; Kochi, Takuya; Kakiuchi, Fumitoshi.

:: Journal of Organic Chemistry, 巻 82, 番号 13, 07.07.2017, p. 6503-6510.

研究成果: Article

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abstract = "Ruthenium-catalyzed C-H arylation of aromatic nitriles with arylboronates is described. The use of RuH2(CO){P(4-MeC6H4)3}3 as a catalyst provided higher yields of the ortho arylation products than the conventional RuH2(CO)(PPh3)3 catalyst. The arylation takes place mostly at the ortho positions, but unprecedented para arylation was also partially observed to give ortho,para diarylation products. In addition to C-H bond cleavage, the cyano group was also found to function as a directing group for cleavage of C-O bonds in aryl ethers.",
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AU - Kakiuchi, Fumitoshi

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AB - Ruthenium-catalyzed C-H arylation of aromatic nitriles with arylboronates is described. The use of RuH2(CO){P(4-MeC6H4)3}3 as a catalyst provided higher yields of the ortho arylation products than the conventional RuH2(CO)(PPh3)3 catalyst. The arylation takes place mostly at the ortho positions, but unprecedented para arylation was also partially observed to give ortho,para diarylation products. In addition to C-H bond cleavage, the cyano group was also found to function as a directing group for cleavage of C-O bonds in aryl ethers.

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