Organic Letters
Letter
Author Contributions
Scheme 5. Double C-Alkylation of 2,5-Dimethylpyrazine
with Benzyl Alcohol (2a)
M.O. established the reaction system and drafted the original
manuscript. K.F. conceptualized, supervised, financed, reviewed,
and edited the manuscript.
Notes
The authors declare no competing financial interest.
a
ACKNOWLEDGMENTS
Reaction was carried out with 2,5-dimethylpyrazine (0.5 mmol), 2a
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(1.0 mmol), [Cp*IrCl2]2 (1.0 mol %), KOtBu (0.5 mmol), 18-crown-
This work was supported by The Research Grant against Global
Warming of the Ichimura Foundation for New Technology.
This work was also financially supported by JSPS KAKENHI
grant numbers JP18H04255, JP19H02715, and JP19H05053.
b
6-ether (0.5 mmol), and THF (1.0 mL) at 120 °C for 20 h. Isolated
yield.
Scheme 6. Reaction Mechanism for the C-Alkylation of
Methylated N-Heteroaromatic Compounds with Primary
Alcohols Based on the Hydrogen-Borrowing Process
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge at
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General experimental procedures and spectroscopic data
for the corresponding products, characterization data, and
AUTHOR INFORMATION
Corresponding Author
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Ken-ichi Fujita − Graduate School of Human and Environmental
Studies, Kyoto University, Kyoto 606-8501, Japan; orcid.org/
Author
Mitsuki Onoda − Graduate School of Human and Environmental
Studies, Kyoto University, Kyoto 606-8501, Japan
Complete contact information is available at:
(13) In each of the previously reported catalytic systems (refs 7−12),
only a few kinds of substrates among 4-methylpyrimidine, 2-
D
Org. Lett. XXXX, XXX, XXX−XXX