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

Department of Chemistry

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

20 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1163-1167
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	695
Issue number	8
DOIs	https://doi.org/10.1016/j.jorganchem.2010.01.022
Publication status	Published - 2010 Apr 15

Keywords

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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Access to Document

10.1016/j.jorganchem.2010.01.022

Cite this

@article{264f9afd7c4a4bb28284f7f73a7db909,

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.",

year = "2010",

month = apr,

day = "15",

doi = "10.1016/j.jorganchem.2010.01.022",

language = "English",

volume = "695",

pages = "1163--1167",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "8",

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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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DO - 10.1016/j.jorganchem.2010.01.022

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JF - Journal of Organometallic Chemistry

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