Phosphine-catalyzed [3+2] cycloaddition of Morita—Baylis—Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes

Article abstract of DOI:10.1007/s11172-021-3162-y

An addition of the Morita—Baylis—Hillman (MBH) carbonates to adamantane-containing isothiocyanates was studied. The MBH carbonates react with 1-(4-isothiocyanatophenyl)-adamantane in the presence of triphenylphosphine to give 5-aryl-substituted adamantane

Full text of DOI:10.1007/s11172-021-3162-y

Russian Chemical Bulletin, International Edition, Vol. 70, No. 5, pp. 880—884, May, 2021
880
Phosphine-catalyzed [3+2] cycloaddition of
Morita—Baylis—Hillman carbonates to isothiocyanates
in the synthesis of adamantane-containing trisubstituted aminothiophenes*
I. S. Zenkov,a A. S. Abel,a A. D. Averin,a,b G. M. Butov,c and I. P. Beletskayaa,b
aDepartment of Chemistry, Lomonosov Moscow State University,
3 Build., 1 Leninskie Gory, 119991 Moscow, Russian Federation.
Fax: +7 (495) 939 3618. E-mail: beletska@org.chem.msu.ru
bFrumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences,
4 Build., 31 Leninsky prosp., 119991 Moscow, Russian Federation
cVolzhsky Polytechnic Institute (branch) of Volgograd State Technical University,
42a ul. Engelsa, 404121 Volzhskii, Russian Federation
An addition of the Morita—Baylis—Hillman (MBH) carbonates to adamantane-containing
isothiocyanates was studied. The MBH carbonates react with 1-(4-isothiocyanatophenyl)-
adamantane in the presence of triphenylphosphine to give 5-aryl-substituted adamantane-
containing 2-amino-4-methoxycarbonylthiophenes in 31—59% yields, while 1- and 2-isothio-
cyanatoadamantanes were found unreactive in this reaction.
Key words: thiophene, organocatalysts, phosphines, adamantane, isothiocyanates, Morita—
Baylis—Hillman carbonates.
In recent years, organocatalysis, the use of small mol-
Previously, we investigated different synthetic ap-
proaches to a wide range of adamantane-containing
heterocyclic compounds by palladium-24 and copper-
catalyzed25 amination of the corresponding halo deriva-
tives. We demonstrated the possibility to synthesize
N-substituted adamantane-containing succinimides by
phosphine-catalyzed cycloaddition of ethyl buta-2,3-di-
enoate to the appropriate maleimides.26 Catalytic amin-
ation of halothiophenes has a number of significant limit-
ations, e.g., by the nature of the amination agent and the
substituents.27—30 Therefore, we synthesized adamantane-
containing 2-aminothiophenes by the phosphine catalyzed
cycloaddition of the Morita—Baylis—Hillman (MBH)
carbonates to isothiocyanates.
ecules to catalyze organic transformations, have been
widely developed. In this field of chemistry, special atten-
tion is given to the reactions catalyzed by phosphines1,2
and N-heterocyclic carbenes (NHCs).3,4 It is of note that
phosphines and NHCs were previously widely known to
the researchers mainly as the ligands for metal complex
catalysis. The recent studies showed that phosphine-catal-
yzed reactions could be an efficient tool for the synthesis
of a wide range of organic compounds,2,5—7 e.g., carbo-
and heterocycles.8 For instance, phosphine-catalyzed
reactions provide a one-step access to polysubstituted
thiophenes.9—11 The thiophene derivatives possess differ-
ent valuable properties, they are extensively studied as the
biologically active compounds12—18 and the components
for organic electronic materials.19,20 Adamantane deriva-
tives exhibit different biological activities since rigid
lipophilic adamantane moiety enhances cell membrane
penetration. Therefore, the development of new ap-
proaches of introduction of the adamantane moiety into
organic molecules is of interest for the search of potential
drugs.21—23 The aim of the present work is the study of
phosphine-catalyzed approach to substituted 2-amino-
thiophenes bearing the adamantane moiety.
To study the possibility to synthesize 2-amino thio-
phenes by phosphine-catalyzed cycloaddition, we selected
isothiocyanates 1—3. In these compounds, the isothio-
* Dedicated to Academician of the Russian Academy of Sciences
V. N. Charushin on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 880—884, May, 2021.
1066-5285/21/7005-0880 © 2021 Springer Science+Business Media LLC

Adamantane-containing aminothiophenes
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 5, May, 2021
881
cyanate moiety is attached to different positions of the
adamantane core either directly (compounds 1 and 2) or
via para-phenylene spacer (compound 3).
To reveal the effects of the substituents on the course
of the organocatalytic reactions, we employed the 4-sub-
stituted MBH carbonates 4a—e as the substrates.
give the corresponding allylic alcohols 5a—e. The synthe-
sized compounds were protected by the tert-butoxycarb-
onyl group under the standard conditions that gave com-
pounds 4a—e in the yields from moderate to high. Both
stages are complicated by polymerization of the product
in the presence of DABCO and DMAP. This leads to
a significant dependence of the product yield on the nature
of the substituent in the aromatic cycle that determines
the tendency of the compound to polymerization.
The conditions of the cycloaddition were chosen based
on the published data.10 The reaction was carried out in
refluxing toluene in the presence of phosphine (20 mol.%)
as a catalyst using 0.4 mol L–1 concentrations of the re-
agents (Scheme 2).
R = Cl (a), H (b), Br (c), F (d), OMe (e)
In the case of isothiocyanates 1 and 2, under any con-
ditions used no formation of the target products was ob-
served. The reaction in the presence of either triphen-
ylphosphine or other phosphines (tributylphosphine,
methyldiphenylphosphine) proceeded with complete
conversions of the MBH carbonates and partial conversion
of isothiocyanates but gave only complex mixtures of the
polymerization products.
The MBH carbonates were synthesized from the corres-
ponding benzaldehydes and methyl acrylate in two steps
by common approach31 (Scheme 1). The first step was the
Morita—Baylis—Hillman reaction catalyzed by DABCO,
namely, the addition to the aldehyde carbonyl group to
Scheme 1
In the case of isothiocyanate 3, the target aminothio-
phenes 6 were obtained in the presence of triphenylphos-
phine (Table 1, entries 1 and 6—9). The use of other
phosphines resulted only in the polymerization products
(entries 2 and 3) but gave no target products. No improve-
ment in the yield of the target products was observed
under microwave irradiation conditions (entries 4 and 5).
The reaction was completed within 1.5 h, the products
were isolated by preparative column chromatography. The
target thiophenes 6a,b,d,e were obtained in 48—59% yields
(entries 1, 6, 8, and 9) and only in the case of 4-bromo-
substituted thiophene 6c the isolated yield was lower (31%,
entry 7). Thus, the nature of the substituent in the phenyl
ring has no substantial effect on the reaction course.
The same reaction conditions were used to synthesize
2-amino-4-acetylated thiophenes from the MBH carbon-
Ar = 4-ClC6H4 (a), Ph (b), 4-BrC6H4 (c), 4-FC6H4 (d),
4-MeOC6H4 (e)
Reagents and conditions: i. DABCO, MeOH, ~20 °C, 72 h;
ii. Boc2O, DMAP, CH2Cl2, ~20 °C, 3 h.
Scheme 2
4, 6: R = Cl (a), H (b), Br (c), F (d), OMe (e)
Reagents and conditions: i. PPh3 (20 mol.%), toluene, 110 °C, 1.5 h.

Zenkov et al.
882
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 5, May, 2021
Table 1. Phosphine-catalyzed [3+2] cycloaddition of Morita—
Baylis—Hillman carbonates to isothiocyanate 3
Scheme 4
Entry
R
Catalyst
MBH
carbonate
Product Yield (%)
1
2
3
Cl
Cl
PPh3
PBu3
PMePh2
PPh3
4a
4a
4a
4a
4a
4b
4c
4d
4e
6a
6a
6a
6a
6a
6b
6c
6d
6e
53
0
Cl
0
4a
5b
6
Cl
50
0
50
31
59
48
Cl
PPh3
H
PPh3
7
8
9
Br
PPh3
F
PPh3
OMe
PPh3
a Reaction was carried out under microwave irradiation at 110 °C.
b Reaction was carried out under microwave irradiation at 70 °C.
ate 7 (Scheme 3), which was prepared by the known
procedure.9 However, this reaction gave only isomeric
product 8 in very low yield of 4%.
Scheme 3
thiocyanate could be realized. Apparently, the reactiv-
ity of the nucleophilic centers strongly depends on the
nature of the substituents. In the case of the MBH
carbonates 4a—e, the nucleophilic attack resulted in
5-aryl-2-aminothiophene 6, while in the case of the
MBH 7 another nucleophilic center is involved. It seems
that the methyl group due to the proton transfer and for-
mation of the stable enolate promoted the numerous side
reactions.
Reagents and conditions: PPh3 (20 mol.%), toluene, 110 °C,
1.5 h.
Formation of products 6 and 8 can be rationalized by
analyzing the reaction mechanism (Scheme 4). Addition
of phosphine to the MBH carbonate gave ylide that
eliminated tert-butylcarbonate anion decomposing into
CO2 and tert-butylate anion. Further, the tert-butylate
anion acted as a base that resulted in the formation of the
conjugated ylide.32 This intermediate has two nucleophilic
centers, therefore two directions of the attack by iso-
In summary, in the present work we revealed the
possibilities and limitations of phosphine-catalyzed
[3+2] cycloaddition in the synthesis of adamantane-

Adamantane-containing aminothiophenes
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 5, May, 2021
883
Yield 44 mg (50%), yellow powder. M.p. 146—147 °C. 1H NMR
(CDCl3), δ: 1.74—1.82 (m, 6 H, HAd); 1.89—1.91 (m, 6 H, HAd);
containing 5-aryl-4-methoxycarbonyl-2-aminothio-
phenes. These peculiarities were used to synthesize
a broader range of adamantane-containing thiophene
derivatives.
2.10 (br.s, 3 H, HAd); 3.73 (s, 3 H, OMe); 6.98 (d, 2 H, HAr
,
3J = 8.6 Hz); 7.07 (s, 1 H, HThio); 7.28 (d, 2 H, HAr, 3J = 8.3 Hz);
7.37—7.42 (m, 3 H, HAr); 7.49—7.52 (m, 2 H, HAr); the NH
group proton signal was not ambiguously attributed. 13C NMR
(CDCl3), δ: 28.9 (3 C, CAd); 35.6 (1 C, CAd); 36.8 (3 C, CAd);
43.3 (3 C, CAd); 51.5 (1 C, OMe); 115.2 (2 C), 118.4 (1 C), 125.8
(2 C), 125.9 (1 C), 127.9 (2 C), 128.3 (1 C), 129.7 (2 C), 133.3
(1 C), 141.9 (1 C), 142.5 (1 C), 144.1 (1 C), 144.9 (1 C), 163.7
(1 C, C(O)). MS (MALDI, PEG-400), found: m/z 444.201
[M + H]+. Calculated for C28H30NO2S: 444.199.
Methyl 5-{[4-(adamantan-1-yl)phenyl]amino}-2-(4-bromo-
phenyl)thiophene-3-carboxylate (6c) was synthesized from MBH
carbonate 4c (74 mg, 0.20 mmol) and compound 3 (65 mg,
0.24 mmol) in the presence of PPh3 (11 mg, 0.04 mmol) in
toluene 0.5 mL. Eluent for CC was PE—CH2Cl2 (1 : 1). Yield
32 mg (31%), yellow oil. 1H NMR (CDCl3), δ: 1.72—1.80 (m, 6 H,
Experimental
1H and 13C NMR spectra were run on a Bruker Avance-400
instrument (working frequencies of 400 (1H) and 100 MHz (13C))
at 298 K. 19F NMR spectra were recorded with an Agilent 400-MR
instrument (working frequency of 376 MHz). Matrix-assisted
laser desorption/ionization (MALDI) mass spectrometry was
performed with a Bruker Ultraflex-II instrument using 1,8,9-tri-
hydroxyanthracene as a matrix and polyethylene glycols as the
internal standards. Microwave experiments were carried out using
an Anton Paar Monowave 400 high-performance microwave
reactor. For preparative column chromatography (CC), Merck
silica gel (40/60) was used. Adamantane-containing isothiocyan-
ates 1—3 were synthesized from the corresponding amines as
earlier described.33 The Morita—Baylis—Hillman carbonates
4a—e were synthesized from methyl acrylate and the appropriate
aldehydes following the known procedure.31 Compound 7 was
synthesized in two steps from methyl vinyl ketone and 4-chloro-
benzaldehyde as earlier described.9 Triphenylphosphine (Aldrich)
was used as purchased. Toluene was distilled over sodium metal
under an argon atmosphere. Petroleum ether (PE), dichloro-
methane, and methanol were distilled prior to use.
Phosphine-catalyzed [3+2] cycloaddition of the Morita—
Baylis—Hillman carbonate 4a—c to 1-(4-isothiocyanatophenyl)-
adamantane 3 (general procedure). A two-neck flask equipped
with a magnetic stirrer and a reflux condenser was charged with
the MBH carbonate 4 (0.20 mmol), PPh3 (20 mol.%, 11 mg,
0.04 mmol), and 1-(4-isothiocyanatophenyl)adamantane 3
(65 mg, 0.24 mmol). The flask was flushed with argon and an-
hydrous toluene (0.5 mL) was added under stream of argon. The
mixture was stirred at 110 °C for 1.5 h under argon. The solvent
was removed in vacuo, product was purified by CC using gradient
elution with PE→PE—CH2Cl2 (4 : 1 → 1 : 1).
H
Ad); 1.87—1.89 (m, 6 H, HAd); 2.09 (br.s, 3 H, HAd); 3.73
(s, 3 H, OMe); 6.96 (d, 2 H, HAr
,
3J = 8.6 Hz); 7.03 (s, 1 H,
HThio); 7.27 (m, 2 H, HAr); 7.36 (m, 2 H, HAr); 7.48—7.53
(m, 2 H, HAr); the NH group proton signal was not ambigu-
ously attributed. 13C NMR (CDCl3), δ: 28.9 (3 C, CAd); 35.6
(1 C, CAd); 36.8 (3 C, CAd); 43.3 (3 C, CAd); 51.6 (1 C, OMe);
115.3 (2 C), 118.0 (1 C), 122.6 (1 C), 125.8 (2 C), 131.1 (2 C),
131.3 (2 C), 132.3 (1 C), 133.3 (1 C), 140.5 (1 C), 141.7 (1 C),
144.3 (1 C), 145.5 (1 C), 163.5 (1 C, C(O)). MS (MALDI,
PEG-400), found: m/z 522.110 [M + H]+. Calculated for
C28H29BrNO2S: 522.110.
Methyl 5-{[4-(adamantan-1-yl)phenyl]amino}-2-(4-fluoro-
phenyl)thiophene-3-carboxylate (6d) was synthesized from MBH
carbonate 4d (62.0 mg, 0.20 mmol) and compound 3 (65 mg,
0.24 mmol) in the presence of PPh3 (11 mg, 0.04 mmol) in
toluene (0.5 mL). Eluent for CC was PE—CH2Cl2 (1 : 1). Yield
1
54.4 mg (59%), yellow powder. M.p. 162—163 °C. H NMR
(CDCl3), δ: 1.76—1.84 (m, 6 H, HAd); 1.92—1.94 (m, 6 H, HAd);
2.13 (br.s, 3 H, HAd); 3.77 (s, 3 H, OMe); 5.71 (br.s, 1 H, NH);
6.99 (d, 2 H, HAr, 3J = 8.6 Hz); 7.07—7.13 (m, 3 H, HThio, HAr);
7.30 (d, 2 H, HAr,
3J = 8.6 Hz); 7.49—7.52 (m, 2 H, HAr).
Methyl 5-{[4-(adamantan-1-yl)phenyl]amino}-2-(4-chloro-
phenyl)thiophene-3-carboxylate (6a) was synthesized from MBH
carbonate 4a (65.3 mg, 0.20 mmol) and compound 3 (65 mg,
0.24 mmol) in the presence of PPh3 (10.5 mg, 0.04 mmol) in
toluene (0.5 mL). Eluent for CC was PE—CH2Cl2 (2 : 1) →
→ PE—CH2Cl2 (1 : 1). Yield 50.6 mg (53%), yellow powder.
13C NMR (CDCl3), δ: 29.0 (3 C, CAd); 35.6 (1 C, CAd); 36.8
(3 C, CAd); 43.3 (3 C, CAd); 51.6 (1 C, OMe); 115.0 (d, 2 C,
2JC—F = 21.9 Hz), 115.2 (2 C), 118.2 (1 C), 125.8 (2 C), 128.6
(1 C), 129.3 (1 C), 131.6 (d, 2 C, 3JC—F = 8.4 Hz), 132.2 (1 C),
141.3 (1 C), 143.1 (d, 1 C, 1JC—F = 225.9 Hz), 145.1 (1 C), 163.5
(1 C), 164.0 (1 C). 19F NMR (CDCl3), δ: –113.30 (tt, 1 F,
J = 8.6 Hz, J = 5.4 Hz). MS (MALDI, PEG-400), found: m/z
462.191 [M + H]+. Calculated for C28H29FNO2S: 462.190.
Methyl 5-{[4-(adamantan-1-yl)phenyl]amino}-2-(4-meth-
oxyphenyl)thiophene-3-carboxylate (6e) was synthesized from
MBH carbonate 4e (65 mg, 0.20 mmol) and compound 3 (65 mg,
0.24 mmol) in the presence of PPh3 (11 mg, 0.04 mmol) in
toluene (0.5 mL). Eluent for CC was PE—CH2Cl2 (1 : 1) →
→ CH2Cl2. Yield 45.4 mg (48%), yellow powder. M.p.
1
M.p. 108—109 °C. H NMR (CDCl3), δ: 1.73—1.81 (m, 6 H,
HAd); 1.88—1.91 (m, 6 H, HAd); 2.09 (br.s, 3 H, HAd); 3.73
(s, 3 H, OMe); 5.75 (br.s, 1 H, NH); 6.96 (d, 2 H, HAr
,
3J = 8.6 Hz), 7.03 (s, 1 H, HThio); 7.25—7.28 (m, 2 H, HAr);
7.33—7.36 (m, 2 H, HAr); 7.41—7.44 (m, 2 H, HAr). 13C NMR
(CDCl3), δ: 28.9 (3 C, CAd); 35.6 (1 C, CAd); 36.7 (3 C, CAd);
43.3 (3 C, CAd); 51.6 (1 C, OMe); 115.2 (2 C), 117.9 (1 C), 125.8
(2 C), 128.1 (2 C), 128.4 (1 C), 131.1 (2 C), 131.5 (1 C), 132.2
(1 C), 134.3 (1 C), 141.8 (1 C), 144.2 (1 C), 145.5 (1 C), 163.5
(1 C, C(O)). MS (MALDI, PEG-300), found: m/z 478.163
[M + H]+. Calculated for C28H29ClNO2S: 478.161.
1
158—159 °C. H NMR (CDCl3), δ: 1.73—1.81 (m, 6 H, HAd);
1.89—1.91 (m, 6 H, HAd); 2.10 (br.s, 3 H, HAd); 3.74 (s, 3 H,
OMe); 3.84 (s, 3 H, OMe); 5.66 (br.s, 1 H, NH); 6.90—6.96
(m, 4 H, HAr); 7.04 (s, 1 H, HThio); 7.26 (d, 2 H, HAr, 3J = 8.6 Hz);
Methyl 5-{[4-adamantan-1-yl)phenyl]amino}-2-phenylthio-
phene-3-carboxylate (6b) was synthesized from MBH carbonate
4b (58 mg, 0.2 mmol) and compound 3 (65 mg, 0.24 mmol) in
the presence of PPh3 (11 mg, 0.04 mmol) in toluene (0.5 mL).
Eluent for CC was PE—CH2Cl2 (2 : 1) → PE—CH2Cl2 (1 : 1).
7.44 (d, 2 H, HAr,
3J = 8.6 Hz). 13C NMR (CDCl3), δ: 28.9
(3 C, CAd); 35.6 (1 C, CAd); 36.8 (3 C, CAd); 43.3 (3 C, CAd);
51.5 (1 C, OMe); 55.3 (1 C, OMe); 113.4 (2 C), 114.9 (2 C),
118.7 (1 C), 125.3 (1 C), 125.6 (1 C), 125.7 (2 C), 131.0 (2 C),

Zenkov et al.
884
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 5, May, 2021
142.2 (1 C), 143.0 (1 C), 143.8 (1 C), 144.2 (1 C), 159.7 (1 C,
C—O); 163.7 (1 C, C(O)). MS (MALDI, PEG-400), found:
m/z 474.210 [M + H]+. Calculated for C29H32NO3S: 474.195.
1-[5-{[4-(Adamantan-1-yl)phenyl]amino}-4-(4-chlorophen-
yl)thiophen-3-yl]ethanone (8) was synthesized from MBH carb-
onate 7 (62 mg, 0.20 mmol) and compound 3 (65 mg, 0.24 mmol)
in the presence of PPh3 (11 mg, 0.04 mmol) in toluene (0.5 mL).
Eluent for CC was PE—CH2Cl2 (1 : 1). Yield 4 mg (4%), yellow oil.
1H NMR (CDCl3), δ: 1.72—1.80 (m, 6 H, HAd); 1.85—1.92 (m, 6 H,
HAd); 2.09 (br.s, 3 H, HAd); 2.33 (s, 3 H, CH3); 6.91 (d, 2 H,
HAr, 3J = 8.6 Hz); 7.18—7.20 (m, 2 H, HAr); 7.23—7.25 (m, 2 H,
14. C. Doebelin, R. Patouret, R. D. Garcia-Ordonez, M. R.
Chang, V. Dharmarajan, S. Novick, A. Ciesla, S. Campbell,
L. A. Solt, P. R. Griffin, T. M. Kamenecka, Bioorg. Med.
Chem. Lett., 2018, 28, 3210.
15. A. Flood, C. Trujillo, G. Sanchez-Sanz, B. Kelly, C. Mugu-
ruza, L. F. Callado, I. Rozas, Eur. J. Med. Chem., 2017,
138, 38.
16. H. Fujieda, M. Kogami, M. Sakairi, N. Kato, M. Makino,
N. Takahashi, T. Miyazawa, S. Harada, T. Yamashita, Eur.
J. Med. Chem., 2018, 156, 269.
17. V. B. Sokolov, A. Yu. Aksinenko, A. V. Gabrel´yan, V. V.
Grigoriev, Russ. Chem. Bull., 2019, 68, 1629; DOI: 10.1007/
s11172-019-2602-4.
18. V. V. Dotsenko, D. S. Buryi, D. Yu. Lukina, S. G. Krivokolysko,
Russ. Chem. Bull., 2020, 69, 1829; DOI: 10.1007/s11172-020-
2969-2.
19. F. A. Larik, M. Faisal, A. Saeed, Q. Abbas, M. A. Kazi,
N. Abbas, A. A. Thebo, D. M. Khan, P. A. Channar, J. Mater.
Sci.: Mater. Electron., 2018, 29, 17975.
3
HAr); 7.36 (d, 2 H, HAr, J = 8.6 Hz); 7.59 (s, 1 H, HThio); the
NH group proton signal was not ambiguously attributed. 13C NMR
(CDCl3), δ: 28.5 (1 C, CH3); 28.9 (3 C, CAd); 36.7 (3 C, CAd);
43.3 (3 C, CAd); 115.5 (2 C), 123.8 (1 C), 125.8 (2 C), 128.8
(2 C), 131.2 (2 C), the quaternary carbon signals were nor at-
tributed due to their low intensity. MS (MALDI, PEG-400),
found: m/z 462.173 [M + H]+. Calculated for C28H29ClNOS:
462.166.
20. E. I. Zhilyaeva, G. V. Shilov, S. A. Torunova, A. M. Flakina,
K. V. Van, R. N. Lyubovskaya, Russ. Chem. Bull., 2019, 68,
1350; DOI: 10.1007/s11172-019-2561-9.
21. L. Wanka, K. Iqbal, P. R. Schreiner, Chem. Rev., 2013,
113, 3516.
22. V. B. Sokolov, A. Yu. Aksinenko, T. A. Epishina, T. V. Goreva,
Russ. Chem. Bull., 2019, 68, 1424; DOI: 10.1007/s11172-019-
2571-7.
This work was financially supported by the Russian
Science Foundation (Project No. 19-13-00223).
This work does not involve human participants and
animal subjects.
The authors declare no conflicts of interests.
23. E. V. Suslov, K. Yu. Ponomarev, D. V. Korchagina, K. P.
Volcho, N. F. Salakhutdinov, Russ. Chem. Bull., 2019, 68,
601; DOI: 10.1007/s11172-019-2461-z.
24. A. S. Abel, A. D. Averin, A. K. Buryak, E. N. Savelyev, B. S.
Orlinson, I. A. Novakov, I. P. Beletskaya, Synthesis, 2017,
49, 5067.
25. A. S. Abel, A. D. Averin, M. V. Anokhin, O. A. Maloshitskaya,
G. M. Butov, E. N. Savelyev, B. S. Orlinson, I. A. Novakov,
I. P. Beletskaya, Russ. J. Org. Chem., 2015, 51, 301.
26. A. S. Abel, A. D. Averin, E. N. Savelyev, B. S. Orlinson, I. A.
Novakov, I. P. Beletskaya, Mendeleev Commun., 2017, 27, 550.
27. M. W. Hooper, M. Utsunomiya, J. F. Hartwig, J. Org. Chem.,
2003, 68, 2861.
28. Z. Lu, R. J. Twieg, Tetrahedron, 2005, 61, 903.
29. Z. Lu, R. J. Twieg, S. D. Huang, Tetrahedron Lett., 2003, 44, 6289.
30. T. J. Luker, H. G. Beaton, M. Whiting, A. Mete, D. R.
Cheshire, Tetrahedron Lett., 2000, 41, 7731.
References
1. H.-G. Dan, G.-W. Rao, Russ. J. Org. Chem., 2018, 54, 815.
2. H. Guo, Y. C. Fan, Z. Sun, Y. Wu, O. Kwon, Chem. Rev.,
2018, 118, 10049.
3. S. Mondal, S. R. Yetra, S. Mukherjee, A. T. Biju, Acc. Chem.
Res., 2019, 52, 425.
4. Q. Ren, M. Li, L. Yuan, J. Wang, Org. Biomol. Chem., 2017,
15, 4731.
5. A. V. Il´in, A. R. Fatkhutdinov, A. V. Salin, Phosphorus, Sulfur
Silicon Relat. Elem., 2016, 191, 1628.
6. E. I. Musina, A. S. Balueva, A. A. Karasik, in Organophosphorus
Chemistry, Eds D. W. Allen, D. Loakes, J. C. Tebby, The
Royal Society of Chemistry, 2019, Vol. 48, pp. 1—63.
7. A. V. Salin, A. V. Il´in, Phosphorus, Sulfur Silicon Relat. Elem.,
2019, 194, 355.
8. Y. Huang, J. Liao, W. Wang, H. Liu, H. Guo, Chem. Commun.,
2020, 56, 15235.
9. X.-Y. Guan, M. Shi, ACS Catal., 2011, 1, 1154.
10. K. H. Kim, J. W. Lim, S. Y. Kim, J. N. Kim, Tetrahedron
Lett., 2015, 56, 5799.
11. D. Virieux, A.-F. Guillouzic, H.-J. Cristau, Heteroat. Chem.,
2007, 18, 312.
31. X. Companyó, P.-Y. Geant, A. Mazzanti, A. Moyano, R. Rios,
Tetrahedron, 2014, 70, 75.
32. N.-J. Zhong, Y.-Z. Wang, L. Cheng, D. Wang, L. Liu, Org.
Biomol. Chem., 2018, 16, 5214.
33. V. V. Burmistrov, G. M. Butov, D. A. Pitushkin, Russ. J. Org.
Chem., 2015, 51, 1795.
12. D. Barrus, A. M. Decker, T. F. Gamage, T. L. Langston,
J.-X. Li, T. Nguyen, B. F. Thomas, Y. Zhang, J. Med. Chem.,
2019, 62, 9806.
13. H. Cheng, X. Li, C. Wang, Y. Chen, S. Li, J. Tan, B. Tan,
Y. He, Cancer Lett., 2019, 443, 80.
Received January 18, 2021;
in revised form February 18, 2021;
accepted February 21, 2021