C
Synlett
A. Mihoya et al.
Letter
Tip
Ar
OR
P OR
OR
References and Notes
TeO
Tip
hν
3O2
1O2
(1) Mukaiyama, T.; Mitunobu, O.; Obata, T. J. Org. Chem. 1965, 30,
rose
bengal
and/or
TeO2
–
PF6
Ar =
101.
Ar
+
N
(2) Motoshima, K.; Sato, A.; Yorimitu, H.; Oshima, K. Bull. Chem. Soc.
N
OR
+
Jpn. 2007, 80, 2229.
Tip
Ar
–
TipTeAr (5)
Te
O
P
OR
i-Pr
i-Pr
(3) (a) Marino, M. P.; Placek, D. C. In Synthetic Lubricants and High-
Performance Functional Fluids, 2nd ed; Rudnick, L. R.; Shubkin,
R. L., Ed.; Marcel Decker: New York, 1999, Chap. 3, 103. (b) Moy,
P. J. Vinyl Addit. Technol. 2004, 10, 187. (c) Barr, D. B.; Bravo, R.;
Weerasekera, G.; Caltabiano, L. M.; Whitehead, R. D. Jr.; Olsson,
A. O.; Caudill, S. P.; Schober, S. E.; Pirkle, J. L.; Sampson, R. J.;
Needham, L. L. Environ. Health Perspect. 2004, 112, 186.
OR
A
Tip =
i-Pr
OR
OR
OR
O
P
Scheme 2 Plausible reaction mechanism for the catalytic oxidation of
phosphite esters
(
d) Oldenhoveda de Guertechin, L. In Handbook of Detergents,
Part A: Properties; Broze, G., Ed.; Marcel Dekker: New York,
999, Chap. 2, 18.
1
(
(
(
(
(
4) Okada, Y.; Oba, M.; Arai, A.; Tanaka, K.; Nishiyama, K.; Ando, W.
Inorg. Chem. 2010, 49, 383.
5) Oba, M.; Tanaka, K.; Nishiyama, K.; Ando, W. J. Org. Chem. 2011,
76, 4173.
6) Oba, M.; Okada, Y.; Nishiyama, K.; Shimada, S.; Ando, W. Chem.
Commun. 2008, 5378.
7) Oba, M.; Okada, Y.; Nishiyama, K.; Ando, W. Org. Lett. 2009, 11,
Table 3 Recycling of Catalyst 5a
RB, 5 (20 mol%), hν
O
P
OPh
PhO
P
OPh
PhO
OPh
OPh
(bmim)[PF ], 15 °C, 2.5 h
6
Cycle
1
2
3
4
5
1879.
Yield (%)
99
quant
quant
quant
quant
8) (a) Koguchi, S. Trans. Mater. Res. Soc. Jpn. 2013, 38, 35.
a
Reaction conditions: (PhO)
] (5 mL), LED (60 W), in air, 2.5 h, 15 °C.
3
P (0.25 mmol), 5 (0.05 mmol), RB (0.0125
(b) Koguchi, S.; Nakamura, K. Synlett 2013, 24, 2305.
(c) Koguchi, S.; Izawa, K. ACS Comb. Sci. 2014, 16, 381.
(d) Koguchi, S.; Mihoya, A.; Mimura, M. Tetrahedron 2016, 72,
mmol), (bmim)[PF
6
In summary, we have developed a hydrophobic ionic-
liquid-supported bulky diaryltelluride 5 and demonstrated
its catalytic utility in the aerobic oxidation of phosphite es-
7633. (e) Koguchi, S.; Shibuya, Y.; Igarashi, Y.; Takemura, H.
Synlett 2019, 30, 943.
(9) Mihoya, A.; Koguchi, S.; Shibuya, Y.; Mimura, M.; Oba, M. Cata-
lysts 2020, 10, 398.
10) Triphenyl Phosphate (Table 2, Entry 1); Typical Procedure
1
0
ters. This system exhibits a desirable catalytic perfor-
mance and a low environmental footprint due to its ability
to be recycled.
(
A solution of (PhO) P (0.0773 g, 0.250 mmol) in (bmim)[PF ] (5
3
6
mL) containing 5 (0.0330 g, 0.0500 mmol) and rose bengal
0.0128 g, 0.0125 mmol) was vigorously stirred in an open flask
(
and irradiated with a 60 W LED lamp for 2.5 h. The temperature
was kept at about 15 °C by using an ice bath during the irradia-
Supporting Information
tion. The resulting mixture was extracted with Et O, and the
solvent was then evaporated to give a pink solid; yield: 0.0803 g
2
Supporting Information for this article is available online at
https://doi.org/10.1055/s-0040-1706068.
S
u
p
p
ortingInform ati
o
nS
u
p
p
ortingInformati
o
n
(
99%); mp 44–47 °C.
1
H NMR (500 MHz, CDCl ): = 7.36 (t, J = 7.7, 6 H), 7.25–7.19
3
3
(
m, 9 H). 1 C NMR (125 MHz, CDCl ): = 150.6, 150.5, 130.0,
3
1
(
25.7, 120.3, 120.2. 31P NMR (202 MHz, CDCl ): = –17.7. HRMS
3
APCI): m/z [M + H]+ calcd for C18H16O P: 327.0781; found:
4
327.0743.
©
2020. Thieme. All rights reserved. Synlett 2020, 32, A–C