RuH2(CO)(PPh3)3-catalyzed arylation of aromatic esters using arylboronates via C-H bond cleavages

Kentaroh Kitazawa; Masashi Kotani; Takuya Kochi; Michael Langeloth; Fumitoshi Kakiuchi

doi:10.1016/j.jorganchem.2010.01.022

RuH₂(CO)(PPh₃)₃-catalyzed arylation of aromatic esters using arylboronates via C-H bond cleavages

Kentaroh Kitazawa, Masashi Kotani, Takuya Kochi, Michael Langeloth, Fumitoshi Kakiuchi

化学科

研究成果: Article › 査読

20 被引用数 (Scopus)

抄録

The RuH₂(CO)(PPh₃)₃-catalyzed C-H functionalization of aromatic esters with 5,5-dimethyl-2-aryl-[1,3,2]dioxaborinanes (arylboronates) gave the ortho arylation products. This coupling reaction can be performed with various combinations of isopropyl benzoate derivatives and arylboronates. Introduction of CF₃ group in the aromatic ring increased the reactivity of the esters. Pinacolone effectively served as an acceptor of a hydride generated by C-H bond cleavage, and the amount of pinacolone used also affected the yield of the arylation product.

本文言語	English
ページ（範囲）	1163-1167
ページ数	5
ジャーナル	Journal of Organometallic Chemistry
巻	695
号	8
DOI	https://doi.org/10.1016/j.jorganchem.2010.01.022
出版ステータス	Published - 2010 4 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

文献へのアクセス

10.1016/j.jorganchem.2010.01.022

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引用スタイル

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title = "RuH2(CO)(PPh3)3-catalyzed arylation of aromatic esters using arylboronates via C-H bond cleavages",

abstract = "The RuH2(CO)(PPh3)3-catalyzed C-H functionalization of aromatic esters with 5,5-dimethyl-2-aryl-[1,3,2]dioxaborinanes (arylboronates) gave the ortho arylation products. This coupling reaction can be performed with various combinations of isopropyl benzoate derivatives and arylboronates. Introduction of CF3 group in the aromatic ring increased the reactivity of the esters. Pinacolone effectively served as an acceptor of a hydride generated by C-H bond cleavage, and the amount of pinacolone used also affected the yield of the arylation product.",

keywords = "2,6-Diarylbenzoic acid, Aromatic esters, Arylboronates, Biaryls, C-H arylation, Ruthenium",

author = "Kentaroh Kitazawa and Masashi Kotani and Takuya Kochi and Michael Langeloth and Fumitoshi Kakiuchi",

note = "Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research ( 21350056 ) from MEXT and by a Grant for Private Education Institute Aid from MEXT.",

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T1 - RuH2(CO)(PPh3)3-catalyzed arylation of aromatic esters using arylboronates via C-H bond cleavages

AU - Kitazawa, Kentaroh

AU - Kotani, Masashi

AU - Kochi, Takuya

AU - Langeloth, Michael

AU - Kakiuchi, Fumitoshi

N1 - Funding Information: This work was supported, in part, by a Grant-in-Aid for Scientific Research ( 21350056 ) from MEXT and by a Grant for Private Education Institute Aid from MEXT.

PY - 2010/4/15

Y1 - 2010/4/15

N2 - The RuH2(CO)(PPh3)3-catalyzed C-H functionalization of aromatic esters with 5,5-dimethyl-2-aryl-[1,3,2]dioxaborinanes (arylboronates) gave the ortho arylation products. This coupling reaction can be performed with various combinations of isopropyl benzoate derivatives and arylboronates. Introduction of CF3 group in the aromatic ring increased the reactivity of the esters. Pinacolone effectively served as an acceptor of a hydride generated by C-H bond cleavage, and the amount of pinacolone used also affected the yield of the arylation product.

AB - The RuH2(CO)(PPh3)3-catalyzed C-H functionalization of aromatic esters with 5,5-dimethyl-2-aryl-[1,3,2]dioxaborinanes (arylboronates) gave the ortho arylation products. This coupling reaction can be performed with various combinations of isopropyl benzoate derivatives and arylboronates. Introduction of CF3 group in the aromatic ring increased the reactivity of the esters. Pinacolone effectively served as an acceptor of a hydride generated by C-H bond cleavage, and the amount of pinacolone used also affected the yield of the arylation product.

KW - 2,6-Diarylbenzoic acid

KW - Aromatic esters

KW - Arylboronates

KW - Biaryls

KW - C-H arylation

KW - Ruthenium

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