Abstract
The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R?B(OCH2CMe2CH2O), R = aryl, alkenyl, and alkyl) resulted in site-selective C?C bond formation. Among the transition metal complexes screened, the RuH2(CO)(PPh3)3 complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe2, OMe, methyl, and vinyl) and -withdrawing (F and CF3) groups reacted with methoxy ketones to give the corresponding coupling products in high yields.
| Original language | English |
|---|---|
| Pages (from-to) | 2706-2707 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 126 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2004 Mar 10 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
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Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds. / Kakiuchi, Fumitoshi; Usui, Mayumi; Ueno, Satoshi; Chatani, Naoto; Murai, Shinji.
In: Journal of the American Chemical Society, Vol. 126, No. 9, 10.03.2004, p. 2706-2707.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Ruthenium-Catalyzed Functionalization of Aryl Carbon-Oxygen Bonds in Aromatic Ethers with Organoboron Compounds
AU - Kakiuchi, Fumitoshi
AU - Usui, Mayumi
AU - Ueno, Satoshi
AU - Chatani, Naoto
AU - Murai, Shinji
PY - 2004/3/10
Y1 - 2004/3/10
N2 - The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R?B(OCH2CMe2CH2O), R = aryl, alkenyl, and alkyl) resulted in site-selective C?C bond formation. Among the transition metal complexes screened, the RuH2(CO)(PPh3)3 complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe2, OMe, methyl, and vinyl) and -withdrawing (F and CF3) groups reacted with methoxy ketones to give the corresponding coupling products in high yields.
AB - The ruthenium-catalyzed reaction of aryl ethers having a carbonyl group at the ortho position to the ether group with organoboronates (R?B(OCH2CMe2CH2O), R = aryl, alkenyl, and alkyl) resulted in site-selective C?C bond formation. Among the transition metal complexes screened, the RuH2(CO)(PPh3)3 complex showed the highest activity. Several aromatic ketones having methoxy or phenoxy groups at the ortho position can also be used in this coupling reaction. A variety of arylboronates containing electron-donating (NMe2, OMe, methyl, and vinyl) and -withdrawing (F and CF3) groups reacted with methoxy ketones to give the corresponding coupling products in high yields.
UR - http://www.scopus.com/inward/record.url?scp=1542377701&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=1542377701&partnerID=8YFLogxK
U2 - 10.1021/ja0393170
DO - 10.1021/ja0393170
M3 - Article
C2 - 14995180
AN - SCOPUS:1542377701
VL - 126
SP - 2706
EP - 2707
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 9
ER -