TY - JOUR
T1 - Iridium-Catalyzed C(sp3)−H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans
AU - Ohmura, Toshimichi
AU - Kusaka, Satoshi
AU - Torigoe, Takeru
AU - Suginome, Michinori
N1 - Funding Information:
The authors thank Dr. Yuuya Nagata for helping X-ray crystallographic analysis. They are also grateful to Mr. Takaya Fujie for helping with kinetics experiments. This work was supported partially by JSPS KAKENHI Grant Numbers JP26288048 for Scientific Research (B) (TO) and JP15H05811 for Scientific Research on Innovative Areas in Precisely Designed Catalysts with Customized Scaffolding (MS). TO also expresses his appreciation for the support by The Kyoto University Research Fund for Senior Scientists (Core) FY2017 and by Asahi Glass Foundation.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/10/8
Y1 - 2019/10/8
N2 - Intramolecular addition of an O-methyl C(sp3)−H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)−H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).
AB - Intramolecular addition of an O-methyl C(sp3)−H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)−H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).
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U2 - 10.1002/adsc.201900749
DO - 10.1002/adsc.201900749
M3 - Article
AN - SCOPUS:85072112406
SN - 1615-4150
VL - 361
SP - 4448
EP - 4453
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
IS - 19
ER -