A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols

Article abstract of DOI:10.1002/cjoc.201400463

A concise synthesis of 2-(2-hydroxyphenyl)acetonitriles has been developed through reaction of trimethylsilyl cyanide and the o-quinone methides in situ generated from 2-(1-tosylalkyl)phenols under basic conditions. In addition, 2-(2-hydroxyphenyl)acetonitriles could be conveniently transformed to benzofuranones.

Full text of DOI:10.1002/cjoc.201400463

COMMUNICATION
DOI: 10.1002/cjoc.201400463
A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via
the o-Quinone Methides Generated from
2-(1-Tosylalkyl)phenols†
Bo Wu, Xiang Gao, Mu-Wang Chen, and Yong-Gui Zhou*
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences,
Dalian, Liaoning 116023, China
A concise synthesis of 2-(2-hydroxyphenyl)acetonitriles has been developed through reaction of trimethylsilyl
cyanide and the o-quinone methides in situ generated from 2-(1-tosylalkyl)phenols under basic conditions. In
addition, 2-(2-hydroxyphenyl)acetonitriles could be conveniently transformed to benzofuranones.
Keywords 2-(2-hydroxyphenyl)acetonitriles, o-quinone methides, 2-(1-tosylalkyl)phenols
Introduction
o-QM intermediates could be conveniently generated
from 2-(1-tosylalkyl)phenols under basic conditions, we
speculated that o-QMs generated in situ could be rapidly
trapped by cyanide anion to allow the formation of
2-(2-hydroxyphenyl)acetonitriles. Herein, we described
a convenient and straightforward protocol for the rapid
synthesis of 2-(2-hydroxyphenyl)acetonitriles through
reaction of trimethylsilyl cyanide and the o-QMs
generated from 2-(1-tosylalkyl)phenols under basic
conditions (Scheme 1).
Nitriles are ubiquitous and prevalent in various bio-
logically active compounds,[1] natural products[2] and
industrial processes (polymer, agrochemicals, dyestuffs
and pigments),[3] and are versatile intermediates for the
synthesis of other functionalized compounds such as
amines, carboxylic acid derivatives, aldehydes, ketones
and N-heterocycles.[4] Therefore, the concise synthesis
of nitriles has received extensive attention in the past
decades and various efficient approaches for the
construction of nitriles have been developed. Common
routes for the preparation of nitriles contain Sandmeyer-
type reaction,[5] cyanation of alkyl or aryl halides,[6]
dehydration of amides or aldoximes,[7] metal-catalyzed
cyanomethylation,[8] oxidation of primary amines,[9]
hydrocyanation of alkenes or alkynes[10] and so on.[11]
However, most of these existed routes have several
drawbacks involving harsh reaction conditions, tedious
processes, limited selectivity and unsatisfactory yields,
impeding their wider application. Hence, developing a
convenient, efficient and easy operating method for the
rapid synthesis of nitriles is still highly desirable.
o-Quinone methides (o-QMs) are a prominent class
of intermediates in numerous chemical and biological
processes.[12] Consequently, several methods have been
successfully developed for the generation of o-QMs,
including tautomerization, oxidation, acid or base
catalysis, thermolysis, photolysis and olefination of
o-quinones.[13,14] Recently, we reported base-induced
desulfonylation of 2-(1-tosylalkyl)phenols to generate
o-QMs and the reaction of o-QMs with sulfur ylides to
afford trans-2,3-dihydrobenzofurans.[15] Considering the
Scheme 1 A concise strategy for the synthesis of 2-(2-hydroxy-
phenyl)acetonitriles
R1
R1
R1
-
CN
Base
Ts
OH
CN
OH
O
o-QM Intermediates
Experimental
General procedure for synthesis of 2-(2-hydroxy-
phenyl)acetonitriles
A reaction mixture of 2-(1-tosylalkyl)phenol 1 (0.40
mmol), trimethylsilyl cyanide (60 μL, 0.48 mmol),
TBAF (1 mol•L－ in THF, 58 μL, 0.058 mmol) and
1
K2CO3 (66 mg, 0.48 mmol) in acetonitrile (4 mL) was
stirred at 80 ℃ for 12 h. The reaction mixture was
cooled to room temperature. Then water (20 mL) was
added to the mixture. The organic layer was separated
and the aqueous layer was extracted with dichloro-
*
E-mail: ygzhou@diep.ac.cn
Received July 9, 2014; accepted August 18, 2014; published online September 15, 2014.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.2014xxxxx or from the author.
Dedicated to Professor Chengye Yuan and Professor Li-Xin Dai on the occasion of their 90th birthdays.
†
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981

Wu et al.
COMMUNICATION
methane (30 mL×3). The combined organic layer was
dried over anhydrous sodium sulfate, concentrated in
vacuo. The crude product was purified by flash chro-
matography on silica gel using petroleum ether and
ethyl acetate to give the desired product 2-(2-hydroxy-
phenyl)acetonitriles 2.
we next sought to investigate the scope of the substrate
generality in present reaction system. As summarized in
Scheme 2, the transformations proceeded very well and
moderate to excellent yields were achieved. For aryl
substituents as R1, electronic property had slight influ-
ence on the yield. For instance, the reactions provided
the desired products 2a and 2g in 94% and 92% yields,
respectively. However, when alkyl moieties were used
as R1, elimination of hydrogen cyanide from the nitrile
products was very facile and that led to the resulting
alkene compounds as the final products. The substitu-
ents on the benzene ring of the phenol did not affect the
reaction. 2-(Phenyl(tosyl)methyl)naphthalen-1-ol 1j was
also a suitable reaction partner and provided the target
product in moderate yield.
2-(2-Hydroxyphenyl)-2-phenylacetonitrile
(2a)
94% yield, pale yellow oil. 1H NMR (400 MHz, CDCl3)
δ: 7.58－7.28 (m, 6H), 7.26－7.04 (m, 3H), 4.31 (brs,
2H); 13C NMR (100 MHz, CDCl3) δ: 153.8, 150.2,
133.6, 130.1, 129.4, 127.6, 126.1, 123.2, 121.2, 117.5,
110.1, 94.4. HRMS calculated for C14H12NO [M＋H]＋
210.0919, found 210.0908.
Results and Discussion
The initial investigation was conducted with 2-(phe-
nyl(tosyl)methyl)phenol 1a and trimethylsilyl cyanide
(TMSCN) in the presence of K2CO3 (1.2 equiv.) and
TBAF (0.12 equiv.) at room temperature. To our delight,
the desired product 2a was isolated in 33% yield (Table
1, Entry 1). Increasing the reaction temperature to 80
℃, the reactivity was effectively improved and high
yield was obtained (Entry 2). The base played a promi-
nent role in the reaction and assisted desulfonylation to
generate o-QM intermediates. Several common inor-
ganic bases, such as Cs2CO3, K3PO4, NaOH and KOtBu,
only delivered the desired product in moderate yields
(Entries 3－6). Further evaluation of solvents revealed
that the transformation was sensitive to the reaction
medium. CH3CN was proved to be the most favorable
solvent giving an excellent yield (Entries 7－9). There-
fore, the optimal conditions for this reaction were estab-
lished by using K2CO3 (1.2 equiv.) as base, TBAF (0.12
equiv.) as initiator and CH3CN as solvent at 80 ℃.
With the aforementioned reaction conditions in hand,
Scheme 2 Scope for the reaction of 2-(1-tosylalkyl)phenols 1
with trimethylsilyl cyanidea
R1
R1
K2CO3, TBAF
CH3CN, 80 oC
Ts
CN
OH
R2
TMSCN
R2
+
OH
1
2
Ph
CN
CN
OH
CN
OH
CN
OH
OH
2a: 94%
2b: 85%
2c: 80%
2d: 82%
OMe
F
CF3
CN
CN
CN
Table 1 Optimization for the reaction of 2-(phenyl(tosyl)methyl)-
phenol 1a with trimethylsilyl cyanidea
OH
OH
OH
2e: 81%
2f: 89%
2g: 92%
Ph
Ph
Base, TBAF
Solvent, T
Ph
Ph
OH Ph
Ts
CN
+
TMSCN
CN
CN
CN
OH
1a
OH
2a
Br
OH
2h: 86%
MeO
OH
2i: 77%
2j: 62%
Entry
Base
Solvent
T
Yieldb/%
33
a Conditions: 1 (0.40 mmol), TMSCN (0.48 mmol), K2CO3 (1.2 equiv.),
TBAF (0.12 equiv.), CH3CN (4 mL), 80 ℃, 12 h. Isolated yields.
1
2
3
4
5
6
7
8
9
K2CO3
K2CO3
Cs2CO3
K3PO4
NaOH
KOtBu
K2CO3
K2CO3
K2CO3
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
Toluene
DMF
r.t.
80 ℃
80 ℃
80 ℃
80 ℃
80 ℃
80 ℃
80 ℃
80 ℃
94
77
54
77
69
36
81
15
Based on the above experimental results and previ-
ous studies on fluoride-triggered autocatalysis mecha-
nism of the Sakurai-Hosomi reaction reported by Dai
and Hou,[16] a plausible mechanism was illustrated in
Scheme 3. Firstly, the fluoride ion serves as an initiator
to generate cyanide anion. Subsequently, the cyanide
anion undergoes Michael addition with o-QM interme-
diate generated in situ to deliver the intermediate I,
which activates trimethylsilyl cyanide to regenerate ac-
tive cyanide anion and afford the intermediate II, fol-
Dioxane
a Conditions: 1a (0.40 mmol), TMSCN (0.48 mmol), base (1.2
equiv.), TBAF (0.12 equiv.), solvent (4 mL), 12 h. Isolated
yields. TMSCN: trimethylsilyl cyanide; TBAF: tetrabutylammo-
nium fluoride.
b
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Chin. J. Chem. 2014, 32, 981—984

A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides
[2] Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597.
lowed by hydrolysis of intermediate II to afford the de-
sired product 2a.
[3] Pollak, P.; Romeder, G.; Hagedorn, F.; Gelbke, H.-P. Nitriles. In Ull-
mann’s Encyclopedia of Industrial Chemistry; Wiley-VCH, Weinheim,
Germany, 2012.
Scheme 3 A plausible mechanism
[4] (a) Rappoport, Z. The Chemistry of the Cyano Group, Interscience Pub-
lishers, London, 1970; (b) Larock, R. C. Comprehensive Organic Trans-
formations: A Guide to Functional Group Preparations, VCH, New
York, 1989; (c) Srimani, D.; Feller, M.; Ben-David, Y.; Milstein, D.
Chem. Commun. 2012, 48, 11853; (d) Gunanathan, C.; Hoelscher, M.;
Leitner, W. Eur. J. Inorg. Chem. 2011, 2011, 3381; (e) Herr, R. J. Bioorg.
Med. Chem. 2002, 10, 3379.
Me3Si CN
-
1a
K2CO3
Ph
Bu4N+
F
- Me3SiF
H2O
CN
2a
Ph
+
-
OSiMe3
Bu4N
CN
II
[5] (a) Sandmeyer, T. Ber. Dtsch. Chem. Ges. 1884, 17, 1633; (b) Sand-
meyer, T. Ber. Dtsch. Chem. Ges. 1885, 18, 1496; (c) Sandmeyer, T. Ber.
Dtsch. Chem. Ges. 1885, 18, 1492; (d) Hodgson, H. H. Chem. Rev. 1947,
40, 251; (e) Galli, C. Chem. Rev. 1988, 88, 765; (f) Bohlmann, R. In
Comprehensive Organic Synthesis, Eds.: Trost, B. M.; Fleming, I., Per-
gamon, Oxford, U. K., 1991; Vol. 6, p. 203.
O
Ph
o-QMs
CN
Me3Si CN
+
-
O NBu4
I
[6] (a) Rosenmund, K. W.; Struck, E. Ber. Dtsch. Chem. Ges. 1919, 52, 1749;
(b) Lindley, J. Tetrahedron 1984, 40, 1433.
[7] (a) Yamaguchi, K.; Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Mizuno, N.
Angew. Chem., Int. Ed. 2007, 46, 3922; (b) Ishihara, K.; Furuya, Y.;
Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2983; (c) Yan, P.;
Batamack, P.; Prakash, G. K. S.; Olah, G. A. Catal. Lett. 2005, 101, 141;
(d) Barman, D. C.; Thakur, A. J.; Prajapati, D.; Sandhu, J. S. Chem. Lett.
2000, 1196; (e) Iranpoor, N.; Zeynizadeh, B. Synth. Commun. 1999, 29,
2747; (f) Attanasi, O.; Palma, P.; Serra-Zanetti, F. Synthesis 1983, 741.
[8] (a) Kosugi, M.; Ishiguro, M.; Negishi, Y.; Sano, H.; Migita, T. Chem.
Lett. 1984, 1511; (b) Frejd, T.; Klingstedt, T. Synthesis 1987, 40; (c)
Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330; (d) Wu,
L.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 15824; (e) Velcicky, J.;
Soicke, A.; Steiner, R.; Schmalz, H.-G. J. Am. Chem. Soc. 2011, 133,
6948.
The product, 2-(2-hydroxyphenyl)acetonitrile could
be further transformed into the corresponding benzo-
furanone,[17] which is an essential scaffold in a plethora
of important natural products and shows a wide range of
biological activities. In the presence of hydrogen
chloride, 2-(2-hydroxyphenyl)acetonitrile products 2a－
2c were smoothly converted to benzofuranones 3a－3c
in high yields (Scheme 4).
Scheme 4 Synthesis of benzofuranones 3
R1
R1
O
[9] (a) Murahashi, S.-I.; Imada, Y. In Transition Metals for Organic Synthe-
sis, Eds.: Beller, M.; Bolm, C., Wiley-VCH, Weinheim, Germany, 2008,
p. 497; (b) Porta, F.; Crotti, C.; Cenini, S.; Palmisano, G. J. Mol. Catal.
1989, 50, 333; (c) Kim, J.; Stahl, S. S. ACS Catal. 2013, 3, 1652; (d) Aiki,
S.; Taketoshi, A.; Kuwabara, J.; Koizumi, T.-a.; Kanbara, T. J. Or-
ganomet. Chem. 2011, 696, 1301; (e) Yamaguchi, K.; Mizuno, N. Angew.
Chem., Int. Ed. 2003, 42, 1480; (f) Mori, K.; Yamaguchi, K.; Mizugaki,
T.; Ebitani, K.; Kaneda, K. Chem. Commun. 2001, 461; (g) Tseng, K.-N.
T.; Rizzi, A. M.; Szymczak, N. K. J. Am. Chem. Soc. 2013, 135, 16352.
[10] (a) RajanBabu, T. V. Org. React. 2011, 75, 1; (b) Bini, L.; Müller, C.;
Vogt, D. Chem. Commun. 2010, 46, 8325; (c) Beller, M.; Seayad, J.; Til-
lack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368; (d) Nugent, W.
A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479; (e) Falk, A.;
Goederz, A.-L.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2013, 52, 1576;
(f) Gaspar, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4519.
[11] (a) Laulhe, S.; Gori, S. S.; Nantz, M. H. J. Org. Chem. 2012, 77, 9334; (b)
Kamijo, S.; Hoshikawa, T.; Inoue, M. Org. Lett. 2011, 13, 5928; (c) La-
mani, M.; Prabhu, K. R. Angew. Chem., Int. Ed. 2010, 49, 6622; (d) Oi-
shi, T.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2009, 48,
6286; (e) Rajender Reddy, K.; Uma Maheswari, C.; Venkateshwar, M.;
Prashanthi, S.; Lakshmi Kantam, M. Tetrahedron Lett. 2009, 50, 2050; (f)
Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. Org. Lett. 2009, 11,
2461; (g) Ye, Y.; Wang, Y.; Liu, P.; Han, F. Chin. J. Chem. 2013, 31, 27;
(h) Shen, Y.-C.; Zhang, Y.-M. Chin. J. Chem. 2003, 21, 907; (i) Gardner,
P. D.; Rafsanjani, H. S.; Rand, L. J. Am. Chem. Soc. 1959, 81, 3364; (j)
Merijan, A.; Gardner, P. D. J. Org. Chem. 1965, 30, 3965.
37% HCl (aq.), CH3CN
80 oC
CN
OH
O
2
3
R1
4-MeC6H4
82 (3b)
4-MeOC6H4
Ph
Yield/%
77 (3a)
86 (3c)
Conclusions
In conclusion, we have developed a concise protocol
for the rapid synthesis of 2-(2-hydroxyphenyl)aceto-
nitriles by using trimethylsilyl cyanide and 2-(1-tosylal-
kyl) phenols via the formation of o-QM intermediates
under basic condition to give moderate to excellent
yields. Moreover, 2-(2-hydroxyphenyl)acetonitriles
could be conveniently transformed to benzofuranone
derivatives in the presence of hydrogen chloride.
Acknowledgement
This work was financially supported by the National
Natural Science Foundation of China (21125208 &
20921092) and National Basic Research Program of
China (2010CB833300).
[12] (a) Quinone Methides, Ed.: Rokita, S. E., Wiley, Hoboken, 2009; (b)
Basarić, N.; Mlinarić-Majerski, K.; Kralj, M. Curr. Org. Chem. 2014, 18,
19; (c) Doria, F.; Nadai, M.; Folini, M.; Scalabrin, M.; Germani, L.; Sat-
tin, G.; Mella, M.; Palumbo, M.; Zaffaroni, N.; Fabris, D.; Freccero, M.;
Richter, S. N. Chem.-Eur. J. 2013, 19, 78; (d) Doria, F.; Nadai, M.; Folini,
M.; Di Antonio, M.; Germani, L.; Percivalle, C.; Sissi, C.; Zaffaroni, N.;
Alcaro, S.; Artese, A.; Richter, S. N.; Freccero, M. Org. Biomol. Chem.
2012, 10, 2798; (e) Nadai, M.; Doria, F.; Di Antonio, M.; Sattin, G.;
Germani, L.; Percivalle, C.; Palumbo, M.; Richter, S. N.; Freccero, M.;
References
[1] (a) Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. J.
Med. Chem. 2010, 53, 7902; (b) The Merck Index, 13th ed., Ed.: O’Neil,
M. J., Merck & Co., Rahway, NJ, 2001.
Chin. J. Chem. 2014, 32, 981—984
© 2014 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
983

Wu et al.
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Biochimie 2011, 93, 1328.
Rokita, S. E. J. Am. Chem. Soc. 2006, 128, 11940.
[13] For reviews see: (a) Van de Water, R. W.; Pettus, T. R. R. Tetrahedron
2002, 58, 5367; (b) Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18,
9160.
[15] (a) Chen, M.-W.; Cao, L.-L.; Ye, Z.-S.; Jiang, G.-F.; Zhou, Y.-G. Chem.
Commun. 2013, 49, 1660; (b) Osyanin, V. A.; Osipov, D. V.; Klimochkin,
Y. N. J. Org. Chem. 2013, 78, 5505; (c) Wu, B.; Chen, M.-W.; Ye, Z.-S.;
Yu, C.-B.; Zhou, Y.-G. Adv. Synth. Catal. 2014, 356, 383.
[14] For selected examples see: (a) Angle, S. R.; Yang, W. J. Am. Chem. Soc.
1990, 112, 4524; (b) Bolon, D. A. J. Org. Chem. 1970, 35, 3666; (c) Jurd,
L. Tetrahedron 1977, 33, 163; (d) Arumugam, S.; Popik, V. V. J. Am.
Chem. Soc. 2009, 131, 11892; (e) Basarić, N.; Cindro, N.; Hou, Y.; Žab-
čić, I.; Mlinarić-Majerski, K.; Wan, P. Can. J. Chem. 2011, 89, 221; (f)
Bray, C. D. Org. Biomol. Chem. 2008, 6, 2815; (g) Bray, C. D. Synlett
2008, 2500; (h) Green, J. C.; Jiménez-Alonso, S.; Brown, E. R.; Pettus, T.
R. R. Org. Lett. 2011, 13, 5500; (i) Majumdar, N.; Korthals, K. A.; Wulff,
W. D. J. Am. Chem. Soc. 2012, 134, 1357; (j) Parrick, J. Can. J. Chem.
1964, 42, 190; (k) Pathak, T. P.; Sigman, M. S. J. Org. Chem. 2011, 76,
9210; (l) Percivalle, C.; La Rosa, A.; Verga, D.; Doria, F.; Mella, M.;
Palumbo, M.; Di Antonio, M.; Freccero, M. J. Org. Chem. 2011, 76,
3096; (m) Radomkit, S.; Sarnpitak, P.; Tummatorn, J.; Batsomboon, P.;
Ruchirawat, S.; Ploypradith, P. Tetrahedron 2011, 67, 3904; (n) Rodri-
guez, R.; Moses, J. E.; Adlington, R. M.; Baldwin, J. E. Org. Biomol.
Chem. 2005, 3, 3488; (o) Sullivan, W. W.; Ullman, D.; Shechter, H. Tet-
rahedron Lett. 1969, 10, 457; (p) Weinert, E. E.; Dondi, R.; Col-
loredo-Melz, S.; Frankenfield, K. N.; Mitchell, C. H.; Freccero, M.;
[16] (a) Wang, D.-K.; Zhou, Y.-G.; Tang, Y.; Hou, X.-L.; Dai, L.-X. J. Org.
Chem. 1999, 64, 4233; (b) Biddle, M. M.; Reich, H. J. J. Org. Chem.
2006, 71, 4031.
[17] For selected examples see: (a) Anacardio, R.; Arcadi, A.; D’Anniballe,
G.; Marinelli, F. Synthesis 1995, 831; (b) Ramachandran, P. V.; Chen,
G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205; (c) Nicolaou, K.
C.; Snyder, S. A.; Huang, X.-H.; Simonsen, K. B.; Koumbis, A. E.; Bigot,
A. J. Am. Chem. Soc. 2004, 126, 10162; (d) Ge, H.-M.; Zhu, C.-H.; Shi,
D.-H.; Zhang, L.-D.; Xie, D.-Q.; Ng, J. S. W.; Tan, R.-X. Chem.-Eur. J.
2008, 14, 376; (e) Wada, S.; Hitomi, T.; Tokuda, H.; Tanaka, R. Chem.
Biodivers. 2010, 7, 2303; (f) Nicolaou, K. C.; Kang, Q.; Wu, T. R.; Lim,
C. S.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 7540; (g) Nicolaou,
K. C.; Wu, T. R.; Kang, Q.; Chen, D. Y.-K. Angew. Chem., Int. Ed. 2009,
48, 3440; (h) Chen, L.; Zhou, F.; Shi, T.-D.; Zhou, J. J. Org. Chem. 2012,
77, 4354; (i) Cheng, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.;
Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013,
135, 1236.
(Pan, B.; Fan, Y.)
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