Radical addition of secondary phosphine chalcogenides to allylamine: Atom-economic synthesis of aminopropylphosphine chalcogenides

Article abstract of DOI:10.1134/S1070363213100162

Secondary phosphine sulfides and phosphine selenides react with allylamine under the conditions of radical initiation (UV or AIBN) to form the anti-Markovnikov adducts in up to 93 % yield.

Full text of DOI:10.1134/S1070363213100162

ISSN 1070-3632, Russian Journal of General Chemistry, 2013, Vol. 83, No. 10, pp. 1895–1899. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © N.K. Gusarova, S.I. Verkhoturova, T.I. Kazantseva, S.N. Arbuzova, A.I. Albanov, A.A. Tatarinova, B.A. Trofimov, 2013, published
in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 10, pp. 1688–1692.
Radical Addition of Secondary Phosphine Chalcogenides
to Allylamine: Atom-Economic Synthesis
of Aminopropylphosphine Chalcogenides
N. K. Gusarova, S. I. Verkhoturova, T. I. Kazantseva, S. N. Arbuzova,
A. I. Albanov, A. A. Tatarinova, and B. A. Trofimov
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: boris_trofimov@irioch.irk.ru
Received November 8, 2012
Abstract—Secondary phosphine sulfides and phosphine selenides react with allylamine under the conditions
of radical initiation (UV or AIBN) to form the anti-Markovnikov adducts in up to 93 % yield.
DOI: 10.1134/S1070363213100162
Organic phosphines and phosphine chalcogenides
containing the PCH2CH2CH2NR2 fragment are
efficient P,N-ligands for the design of metal complexes
[1–11] and highly reactive building blocks for organic
and organoelemental synthesis [1, 4, 5, 12–14]. Their
complexes with metals are used, for example, as
catalysts for hydrogenation of alkenes [4], ketones [6,
11] (including enantioselective hydrogenation [6]),
imines [11], as well as in the Heck reaction [1]. Metal
complexes of diphenylaminopropylphosphines of
general formula [M(R1R2N(CH2)3PPh2)2]2+ [M = Pt(II),
Pd(II); R1, R2 = H, Me, Bn, cyclohexyl] were proposed
as potential anticancer drugs [2].
chalcogenides are scarce. The addition of dimethyl-
phosphine oxide [24] and diphenylphosphine oxide
[25] to the double bond of allylamines in the presence
of azobisisobutyronitrile (AIBN) [24] or peroxides
[24], or under UV radiation was briefly reported [25].
In the present work the reaction of radical addition
of secondary phosphine sulfides and phosphine
selenides to allylamine has been first studied with the
aim to elaborate a general and convenient atom-
economic method for the synthesis of functional tertiary
phosphine chalcogenides containing amino group.
We have found that secondary phosphine sulfides
Ia–Ic react with allylamine (the ratio of the reagents
1:2.5–3.5) in dioxane or benzene under UV irradiation
(200-W Hg arc Lamp) or in the presence of AIBN
(3 wt %, 60–65°С) in 1–3 h to form aminopropyl-
phosphine sulfides IIa–IIc in 48–93% preparative
yield (Scheme 1, table).
A convenient approach to the synthesis of the title
aminophosphines is the reaction of radical addition to
the allylamine derivatives of phosphine [15–18] and
the primary [10, 12, 13, 19–22] and secondary
phosphines [3, 23]. At the same time, the data on the
reactions of allylamines with secondary phosphine
Scheme 1.
R
R
R
S
S
UV
NH2
P
P
+
NH2
or AIBN (60_65оС)
R
H
IIa_IIc
Ia_Ic
As can be seen from table, the reaction should be
carried out under UV radiation in dioxane. In the
presence of AIBN the addition proceeds slower and is
less selective (cf. runs 1 and 3). The same effect is
observed at the replacement of dioxane by benzene (cf.
runs 1 and 2).
1895

1896
GUSAROVA et al.
Conditions of the reaction of secondary phosphine sulfides with allylamine
Run
Phosphine sulfide
R
Initiator
Solvent
Dioxane
Time, h
Adduct
Yield a, %
1
2
3
4
5
Ph
Ph
Ph
1
1
2
2
3
70 (48)
60 (35)
64 (42)
96 (93)
92 (66)
Iа
Iа
Iа
Ib
Ic
UV
IIа
IIа
IIа
IIb
IIc
UV
Benzene
Dioxane
Dioxane
Dioxane
AIBN
UV
PhCH2CH2
PhCH(Me)CH2
UV
a
Yield calculated from 31P NMR spectra of the crude product. Preparative yield calculated with respect to the phosphine sulfide R2P(S)H
taken in the reaction is given in parentheses.
A rather low yield of phosphine sulfide IIа in the
Secondary phosphine selenides IIIa, IIIb react
with allylamine under UV radiation (dioxane, 1–2.5 h)
to give adducts IVa, IVb in ~71–76% chemo-
selectivity according to the 31P NMR spectra
(Scheme 2).
reaction of diphenylphosphine sulfide Ia with allyl-
amine (runs 1–3) is due to the formation of side
products as indicated by the presence of signals at 60–
61 ppm (10–12%) and 55–56 ppm (20–26%) in the 31P
NMR spectra of the reaction mixtures.
Scheme 2.
R
R
R
Se
Se
UV
NH2
P
P
+
NH2
dioxane
R
H
IVа, IVb
IIIa, IIIb
R = PhCH2CH2 (a), PhCH(Me)CH2 (b).
The corresponding secondary phosphines Va, Vb
and diselenophosphinates VIa, VIb were also iden-
tified in the reaction mixture. In spite of the fact that their
total contents does not exceed 12–15% (from 31P NMR),
their presence hampers the isolation of the target
aminophosphine selenides IVa, IVb and reduces the
preparative yield to 51–58%. Side products Va, Vb,
VIa, VIb apparently are formed as shown in Scheme 3,
which was described earlier by the example of the reac-
tion of secondary phosphine selenides with amines [26].
Scheme 3.
R
R
Se
NH2
_
H3N+
P
2IIIa, IIIb +
R2PH
+
Se
Vа, Vb
VIа, VIb
R = PhCH2CH2 (a), PhCH(Me)CH2 (b).
Note that secondary phosphine oxides under these
conditions (UV radiation or in the presence of AIBN)
practically do not react with allylamine. This is in
contrast to the results of [24, 25] cited in the intro-
duction but is consistent with the commonly accepted
notions on relatively low reactivity of secondary
phosphine oxides in the reactions of radical addition to
the double bond [27–29].
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 10 2013

RADICAL ADDITION OF SECONDARY PHOSPHINE CHALCOGENIDES TO ALLYLAMINE
1897
Scheme 4.
R
R
R
R
Х
KOH/H2O
PhMe
R
Х
Pn
[PH3/H2]
P
H
P
C6H6
KOH/DMSO
H
Ib, Ic, IIIа, IIIb
R = H, X = S (Ib); R = Me, X = S (Ic); R = H, X = Se (IIIa); R = Me, X = Se (IIIb).
3
It is worth mentioning that the starting secondary
sulfides Ib, Ic and selenides IIIa, IIIb are now
available because they are easily prepared from
elemental phosphorus, styrenes, and elemental
chalcogens [30, 31] (Scheme 4).
(2Н, СН2N, JHH 6.7 Hz), 7.43 m (6H, m-Ph, р-Ph),
7.81 m (4H, o-Ph, JHP 13.0 Hz). 13С NMR, δC, ppm:
3
2
26.21 d (СН2СН2СН2, JСP 2.6 Hz), 30.02 d (СН2Р,
1JСP 57.5 Hz), 42.58 d (СН2N, JСP 17.3 Hz), 128.53 d
3
(Сm, 3JСP 12.2 Hz), 131.01 d (Со, 2JСP 10.3 Hz), 131.38
d (Ср, JСP 3.0 Hz), 132.80 d (Сi, JСP 80.0 Hz). 31Р
NMR, δР, ppm: 43.8. Found, %: С 65.65; Н 6.50; N
5.07; P 10.95; S 11.39. С15Н18NРS. Calculated, %: С
65.43; Н 6.59; N 5.09; P 11.25; S 11.65.
4
1
Therefore, the reaction of free-radical addition of
secondary phosphine sulfides and phosphine selenides
to allylamine was performed for the first time and on
its basis an atom-economic method of synthesis of
aminopropylphosphine chalcogenides, promising
N,P=X (X = S, Se) ligands for the design of metal
complex catalysts of new generation and building
blocks for organoelement synthesis, was elaborated.
3-(Diphenethylphosphorothioyl)propylamine (IIb)
(see table, run 4). The solution of bis(2-phenethyl)phos-
phine sulfide Ib (0.089 g, 0.32 mmol) and allylamine
(0.064 g, 1.12 mmol) in 1 mL of dioxane was placed
into a quartz ampule, flushed with argon, and irra-
diated with UV light for 2 h. The reaction mixture was
passed through a layer of Al2O3 (2 cm) (eluent di-
oxane). Dioxane was removed under a reduced pres-
sure, the residue was dried in a vacuum. 0.099 g (93%)
of 3-(diphenethylphosphorothioyl)propylamine IIb was
obtained as light-yellow oil. 1Н NMR, δH, ppm: 1.72 m
(2Н, СН2СН2СН2), 1.85 m (2H, СН2СН2СН2Р), 2.12
EXPERIMENTAL
1Н, 13C, 31Р, and 77Se NMR spectra were taken on a
Bruker DPX 400 (400.13, 101.61, 161.98 and 76.31
MHz, respectively) in CDCl3, internal references
HMDS (1Н, 13C), Me2Se (77Se), external reference
85% H3PO4 (31P). The assignment of the signals in the
1Н, 13C NMR spectra was based on the 2D homo- and
heteronuclear NMR techniques: COSY, HSQC.
Compounds IIc, IVb, Vb, and VIb consist of three
diastereomers (one pair of enantiomers and two meso-
forms) due to the presence of two asymmetric carbon
atoms and the pseudoasymmetric phosphorus atom.
3
m (4Н, PhСН2СН2Р), 2.73 t (2Н, СН2N, JHН 6.7 Hz),
2.92 m (4Н, СН2Рh), 7.18 m (4H, o-Ph), 7.20 m (2H,
p-Ph), 7.28 m (4Н, m-Ph). 13С NMR, δC, ppm: 26.20 d
(СН2СН2СН2, 2JСP 3.4 Hz), 28.59 d (СН2Ph, 2JСP 2.7 Hz),
1
28.72 d (СН2СН2СН2Р, JСP 50.5 Hz), 32.76 d
1
3
(PhСН2СН2Р, JСP 48.6 Hz), 42.58 d (СН2N, JСP 16.1
Hz), 126.58 (Ср), 128.29 (Со), 128.73 (Сm), 140.64 d
(Сi, 3JСP 13.8 Hz). 31Р NMR, δР, ppm: 49.6. Found, %:
С 68.58; Н 7.86; N 3.99; P 9.18; S 9.48. С19Н26NРS.
Calculated, %: С 68.85; Н 7.91; N 4.23; P 9.34; S
9.67.
3-(Diphenylphosphorothioyl)propylamine (IIа)
(see table, run 1). The solution of diphenylphosphine
sulfide Ia (0.054 g, 0.25 mmol) and allylamine (0.050 g,
0.88 mmol) in 1 mL of dioxane was placed into a quartz
ampule, flushed with argon, and irradiated with UV
light for 1 h. The reaction mixture was passed through
a layer of Al2O3 (2 cm) (eluent dioxane). Dioxane was
removed under a reduced pressure, the residue was
dried in a vacuum. 0.033 g (48%) of 3-(diphenylphos-
phorothioyl)propylamine IIа was obtained as light-
3-[Bis(2-phenylpropyl)phosphorothioyl]propyl-
amine (IIc) (see table, run 5). The solution of bis(2-
phenylpropyl)phosphine sulfide Ic (0.094 g, 0.31 mmol)
and allylamine (0.044 g, 0.77 mmol) in 1 mL of di-
oxane was placed into a quartz ampule, flushed with
argon, and irradiated with UV light for 3 h. The
reaction mixture was passed through a layer of Al2O3
1
yellow oil. Н NMR, δH, ppm: 1.30 br.s (2Н, NH2),
1.72 m (2Н, СН2СН2СН2), 2.49 m (2H, СН2Р), 2.74 t
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 10 2013

1898
GUSAROVA et al.
3.1 Hz), 28.04 d (СН2СН2СН2Р, 1JСP 44.3 Hz), 29.28 d
(2 cm) (eluent dioxane). Dioxane was removed under a
reduced pressure, the residue was dried in a vacuum.
0.063 g (66%) of 3-[bis(2-phenylpropyl)phosphorothio-
yl)propylamine IIc was obtained as light-yellow oil. 1Н
NMR, δH, ppm: 1.12 d, 1.12 d, 1.30 d, 1.33 d (6Н, Me,
3JНН 7.2 Hz), 1.22 m (2Н, СН2СН2СН2), 1.77 m (2Н,
СН2СН2Р), 1.71–2.08 m, 1.82–2.08 m, 1.93–2.08 m
(4Н, С*НСН2Р), 2.31 m, 2.33 m, 2.40 m (2Н, СН2N),
3.02 m, 3.25 m, 3.39 m, 3.41 m (2H, C*H), 7.15–7.26
m (10Н, Ph). 13С NMR, δС, ppm: 24.75 d, 24.85 d,
2
1
(СН2Ph, JСP 2.7 Hz), 32.39 d (PhСН2СН2Р, JСP
3
41.6 Hz), 41.27 d (СН2N, JСP 16.1 Hz), 126.56 (Ср),
3
128.27, 128.67 (Со, Сm), 140.21 d (Сi1, JСP 13.8 Hz).
31Р NMR, δР, ppm: 37.5 (+ satellites: JPSe 696.3 Hz).
77Se NMR, δSe, ppm: –384.2 d (1JSeP 696.3 Hz). Found,
%: С 60.59; Н 7.15; N 3.52; Р 7.90; Se 20.91.
С19Н26NРSe. Calculated, %: С 60.32; Н 6.93; N 3.70;
P 8.19; Se 20.87.
3-[Bis(2-phenylpropyl)phosphoroselenoyl]propyl-
amine (IVb). The solution of bis(2-phenylpropyl)
phosphine selenide IIIb (0.100 g, 0.29 mmol) and
allylamine (0.025 g, 0.44 mmol) in 1 mL of dioxane
was placed into a quartz ampule, flushed with argon,
and irradiated with UV light for 2.5 h. In the 31Р NMR
spectrum of the reaction mixture the signals are ob-
served at –82.61, –81.70, –80.79 ppm (1JPH ~200 Hz),
23.70, 24.69, 26.10 ppm (satellites: 1JPSe ~580 Hz) and
37.96, 38.54 38.78 ppm (satellites: 1JPSe ~690 Hz) from
the secondary phosphine Vb, diselenophosphinate
VIb, and adduct IVb, and unidentified signals at 63–
67 ppm (the content of the target product IVb ~71%).
Dioxane was removed under a reduced pressure, the
residue was reprecipitated from ether into cold hexane.
The formed oil was separated and dried in a vacuum to
give 0.06 g (51%) of 3-[bis(2-phenylpropyl)phos-
phoroselenoyl]propylamine IVb as light-yellow oil. 1Н
NMR, δН, ppm: 1.12 d, 1.12 d, 1.30 d, 1.33 d (6Н, Me,
3JНН 7.0 Hz), 1.23 m (2Н, СН2СН2СН2), 1.77 m (2Н,
СН2СН2Р), 1.70–2.08 m, 1.83–2.07 m, 1.92–2.08 m
(4Н, С*НСН2Р), 2.24 m, 2.34 m, 2.39 m (2Н, СН2N),
3.01 m, 3.26 m, 3.39 m, 3.40 m (2H, C*H), 7.10–7.27
m (10Н, Ph). 13С NMR, δС, ppm: 24.71 d, 24.82 d,
3
24.88 d, 24.97 d (Me, JСP 5.6, 2.2, 4.2 and 2.2 Hz,
respectively), 26.12 d, 26.66 d, 27.03 d (СН2СН2Р,
2JСP 3.6, 4.0 and 4.2 Hz, respectively), 28.63 d, 29.80
1
d, 29.94 d (СН2СН2Р, JСP 48.9, 50.9 and 50.2 Hz,
respectively), 34.29 d, 34.58 d, 34.62 d, 35.05 d (С*Н,
2JСP 2.8, 2.8, 3.0 and 3.3 Hz, respectively), 38.01 d,
1
39.03 d, 39.81 d, 39.94 d (С*НСН2Р, JСP 47.9, 47.2,
48.9 and 49.2 Hz, respectively), 42.42 d, 42.55 d,
42.60 d (СН2N, JСP 17.5, 17.1 and 17.1 Hz,
3
respectively), 126.61, 126.72, 126.75, 126.76 (Ср),
127.09, 127.23, 127.25 (Со), 128.54, 128.59, 128.67,
128.69 (Сm), 145.71 d, 145.95 d, 146.01 d, 146.10 d
(Сi, JСP 4.3, 4.6, 4.7 and 4.2 Hz, respectively). 31Р
3
NMR, δР, ppm: 49.0, 49.1, 49.6. Found, %: С 70.32; Н
8.40; N 3.68; P 8.34; S 9.19. С21Н30NРS. Calculated,
%: С 70.16; Н 8.41; N 3.90; P 8.62; S 8.92.
3-(Diphenylethylphosphoroselenoyl)propylamine
(IVa). The solution of bis(2-phenylethyl)phosphine
selenide IIIa (0.103 g, 0.32 mmol) and allylamine
(0.028 g, 0.49 mmol) in 1 mL of dioxane was placed
into a quartz ampule, flushed with argon, and
irradiated with UV light for 1 h. In the 31P NMR
spectrum of the reaction mixture the signals were
observed at –69.05 ppm (1JPH 199 Hz), 24.85 ppm
(satellites: JPSe 556 Hz), 37.50 ppm (satellites: JPSe
696.3 Hz), from the secondary phosphine Va, diseleno-
phosphinate VIа (identified with the authentic sample
[32]) and adduct IVa, as well as unidentified signals at
65.52 and 66.03 ppm (the ratio of signals 2:2:25:1:3,
respectively). Dioxane was removed under a reduced
pressure. The oily residue was washed with hexane
(3×0.5 mL), the residue was extracted with
isopropanol, isopropanol was removed from the extract
under a reduced pressure to give 0.07 g (58%) of 3-(di-
phenethylphosphoroselenoyl)propylamine IVa as light-
yellow oil. 1Н NMR, δH, ppm: 1.85 m (2Н,
СН2СН2СН2), 1.99 m (2H, СН2СН2СН2Р), 2.19 m
(4Н, PhСН2СН2Р), 2.88 m (6Н, СН2N, СН2Ph), 4.71
br.s (2Н, NH2), 7.16 m (6H, o-Ph, p-Ph), 7.24 m (4Н,
3
24.84 d, 24.94 d (Me, JСP 5.0, 4.6, 3.8 and 4.6 Hz,
1
1
respectively), 24.11 d, 24.17 d, 24.23 d (СН2СН2Р,
2JСP 4.2, 4.2 and 3.8 Hz, respectively), 27.57 d, 28.56
1
d, 28.89 d (СН2СН2Р, JСP 41.8, 44.1 and 43.7 Hz,
respectively), 35.13 d, 35.51 d, 35.57 d, 35.85 d (С*Н,
2JСP 2.3, 2.7, 2.7 and 3.5 Hz, respectively), 37.50 d,
1
38.54 d, 39.45 d (С*НСН2Р, JСP 41.4, 40.3, and
42.1 Hz, respectively), 40.11 d, 40.20 d, 40.40 d (СН2N,
3JСP 19.2, 17.6 and 17.3 Hz respectively), 126.64, 126.72,
126.76 (Ср), 127.14, 127.21, 127.31 (Со), 128.64, 128.69,
128.75 (Сm), 145.32 d, 145.62 d, 145.67 d, 145.78 d
3
(Сi, JСP 3.8, 4.2, 5.0 and 4.2 Hz, respectively). 31Р
NMR, δР, ppm: 38.2 (+ satellites: 1JPSe 691.8 Hz), 38.7
1
1
(+ satellites: JPSe 683.8 Hz), 38.8 (+ satellites: JPSe
696.3 Hz). 77Se NMR, δSe, ppm: –375.6 d (1JSeР
691.8 Hz), –365.4 d (1JSeР 683.8 Hz), –348.9 d (1JSeР
696.3 Hz). Found, %: С 61.81; Н 7.26; N 3.21; P 7.74;
13
2
m-Ph). С NMR, δС, ppm: 25.10 d (СН2СН2СН2, JСP
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 10 2013

RADICAL ADDITION OF SECONDARY PHOSPHINE CHALCOGENIDES TO ALLYLAMINE
1899
13. Oehme, H., Thamm, R., and Leissring, E., J. Prakt.
Chem., 1978, vol. 320, no. 4, p. 600.
14. Lachkova, V., Keck, H., Scopelliti, R., Klaeui, W.,
Varbanov, S., and Haegele, G., Z. für Naturfor. B:
Chem. Sci., 2004, vol. 59, no. 2, p. 221.
Se 19.22. C21H30NPSe. Calculated, %: С 62.06; Н 7.44;
N 3.45; P 7.62; Se 19.43.
ACKNOWLEDGMENTS
15. Stiles, A.R., Rust, F.F., and Vaughan, W.E., J. Amer.
Chem. Soc., 1952, vol. 74, p. 3282.
16. GB Patent no. 673451, 1952; C. A., 1953, vol. 47,
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18. Li, D.-G., Sun, H.-L., Xia, C.-G., and Song, H.-L., Youji
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p. 5138.
20. Arbuzov, B.A., Vinokurova, G.M., and Aleksandro-
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This work was performed with the financial support
from the Russian Foundation for Basic Research (grant
no. 11-03-00286) and the Council on Grants of the
President of the Russian Federation for the State
support of the leading scientific schools (grant no.
NSh-1550-2012.3).
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