Job/Unit: O42660
/KAP1
Date: 03-09-14 18:59:03
Pages: 7
Synthesis of Triarylphosphines by Cross-Coupling
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IR (neat): ν = 698.74, 729.40, 747.87, 794.95, 910.71, 1112.56,
˜
1029–1034.
1187.63, 1431.79, 1457.63, 1478.14, 1585.10, 2217.49, 2931.58,
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3054.00, 3384.08 cm–1. MS (ESI): m/z = 340.4 [M + 1]+.
[5]
5-[2-(Diphenylphosphino)phenyl]-1-methyl-1H-tetrazole
(3o):[13a]
1
White solid (107 mg, 62%). H NMR (400 MHz, CDCl3): δ = 4.24
(s, 3 H), 7.02–7.05 (m, 1 H), 7.25–7.37 (m, 11 H), 7.44–7.48 (m, 1
H), 8.05–8.08 (m, 1 H) ppm. 13C NMR (100 MHz, CDCl3): δ =
39.34, 128.36, 128.44, 128.63, 129.80, 129.87 (d, J = 4 Hz), 131.66
(d, J = 23 Hz), 133.90, 134.10, 134.31, 137.17 (d, J = 11 Hz), 137.56
(d, J = 23 Hz), 164.93 ppm. 31P NMR (162 MHz, CDCl3): δ =
–7.95 ppm. IR (neat): ν = 542.95, 697.42, 748.23, 1035.91, 1120.51,
˜
1191.89, 1363.35, 1431.32, 3055.19 cm–1. MS (ESI): m/z = 345.3 [M
+ 1]+. HRMS: calcd. for C20H18PN4 345.1264; found 345.1260.
Methyldiphenylphosphine (3p):[19] Pale yellow liquid (69 mg, 69%).
1H NMR (400 MHz, CDCl3): δ = 1.57–1.58 (d, J = 4 Hz, 3 H),
7.24–7.29 (m, 6 H), 7.36–7.40 (m, 4 H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 12.40 (d, J = 14 Hz), 128.19, 128.25, 131.94 (d, J =
18 Hz), 140.06 (d, J = 12 Hz) ppm. 31P NMR (162 MHz, CDCl3):
δ = –26.82 ppm. IR (neat): ν = 510.00, 682.13, 651.28, 920.46,
˜
1012.36, 1081.66, 1127.35, 1300.74, 1498.54, 2920.12, 3052.23,
3068.30 cm–1. MS (ESI): m/z = 201.3 [M + 1]+.
Supporting Information (see footnote on the first page of this arti-
cle): Copies of the 1H and 13C NMR spectra for the isolated prod-
ucts.
[6]
[7]
Acknowledgments
The authors are grateful to the Northwest University, Xi’an, P. R.
China (PR13089, NF14020) for financial support.
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