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100 °C for 10 h. Then, the reaction mixture was cooled to room
temperature and N,N′-dimethylethylenediamine (5.2 μL, 0.05 mmol),
Cs2CO3 (164 mg, 0.5 mmol), and the respective halide compound
(0.25 mmol) were added under Ar flow. The suspension was allowed
to heat to 110 °C and stirred overnight. Then, the reaction mixture
was cooled to 0 °C and 3 N methanolic KOH was added slowly. After
the mixture was stirred vigorously for 5 h at room temperature, water
(3 mL) was added and the mixture was extracted with ethyl acetate
which was washed by 1 N HCl solution (aq., 5 mL) and saturated
NaHCO3 solution (aq., 5 mL). Then, the organic phase was dried by
Na2SO4 and concentrated under vacuum. The residue was purified by
silica gel column chromatography.
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(2,6-Dimethylphenyl)diphenylphosphine.6b Yield: 73%. 1H
NMR (300 MHz, CDCl3): δ 7.34−7.09 (m, 11 H), 6.97 (dd, J1 =
2.70 Hz; J2 = 7.5 Hz, 2 H), 2.12 (s, 6 H); 13C NMR (75 MHz,
CDCl3): δ 145.6 (d, J = 15.9 Hz), 136.4 (d, J = 14.0 Hz), 131.8, 131.6,
130.2, 128.1, 128.5, 127.7, 23.9 (d, J = 18.1 Hz); 31P NMR (121 MHz,
CDCl3): δ −14.9; MS (EI): m/z 290.
ASSOCIATED CONTENT
* Supporting Information
Synthesis and spectroscopic data of products. This material is
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S
AUTHOR INFORMATION
Corresponding Author
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Author Contributions
†Y.L. and S.D. contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was supported by the state of Mecklenburg-
Vorpommern and the BMBF. Y.L. is grateful for the support
of a Shanghai Institute of Organic Chemistry (SIOC)-Zhejiang
Medicine joint postdoctoral fellowship.
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