Regioselective Ring-Opening Nucleophilic Addition of Aziridines through Photoredox Catalyst

Article abstract of DOI:10.1002/adsc.201400476

A mild and efficient procedure was developed for the regioselective ring-opening nucleophilic addition reactions of aziridines via visible light photoredox catalysis, that provides a practical synthetic access to 1,2-bifunctional compounds. Furthermore, the regioselective synthesis of non-racemic amino ethers from chiral aziridine could also be achieved under mild conditions. Finally, a possible reaction mechanism was proposed and further supported by control experiments.

Full text of DOI:10.1002/adsc.201400476

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DOI: 10.1002/adsc.201400476
Regioselective Ring-Opening Nucleophilic Addition of Aziridines
through Photoredox Catalyst
Hongnan Sun,a Chao Yang,a Run Lin,a and Wujiong Xiaa,b,*
a
State Key Lab of Urban Water Resource and Environment, the Academy of Fundamental and Interdisciplinary Sciences,
Harbin Institute of Technology, Harbin 150080, Peopleꢀs Republic of China
State Key Lab of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, Peopleꢀs Republic of China
b
Fax : (+86)-451-8640-3760; phone: (+86)-451-8640-3760; e-mail: xiawj@hit.edu.cn
Received: May 13, 2014; Published online: && &&, 0000
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201400476.
Abstract: A mild and efficient procedure was devel-
oped for the regioselective ring-opening nucleophil-
ic addition reactions of aziridines via visible light
photoredox catalysis, that provides a practical syn-
thetic access to 1,2-bifunctional compounds. Fur-
thermore, the regioselective synthesis of non-race-
mic amino ethers from chiral aziridine could also be
achieved under mild conditions. Finally, a possible
reaction mechanism was proposed and further sup-
ported by control experiments.
Scheme 1. Regioselectivity in the ring-opening processes.
(Scheme 1). The availability of a mild and efficient
method thus remains appealing for the regioselective
ring-opening reactions of aziridines. In this regard we
considered that a photocatalytic process would poten-
tially be suitable for the synthesis of 1,2-bifunctional
compounds based on our continuing investigations on
photoredox catalytic reactions.[8]
Keywords: aziridines; photoredox catalysis; regiose-
lective ring opening; visible light
Nowadays, the use of visible light and a photoredox
catalyst such as [RuACHTNUTRGNE(UGN bpy)3]Cl2 has appeared to offer
Aziridines are versatile substrates/building blocks for very promising possibilities to activate molecules and
synthesis of numerous nitrogen-containing biological- promote synthetic transformations.[9] We envisioned
ly compounds of contemporary interest.[1] Their abili- that the amino radical cation generated from oxida-
ty to undergo ring-opening reactions owing to the tive quenching process via visible-light photoredox
strain inherent in the three-membered heterocycle catalysis[10] could lead to ring-opening nucleophilic ad-
and the electronegativity of the heteroatom contrib- dition reactions in which the nucleophiles and hydro-
ute largely to their synthetic value in organic synthe- gen atom would stem from reagent sources.
sis. In the past decades, extensive studies have been
Considering that a judicious selection of the amine
carried out on ring-opening reactions of aziridines protecting group, which is adequately electron-with-
with various nucleophiles,[2] among which most meth- drawing to suppress amine oxidation, could inhibit
ods are mainly focused on catalytic process with undesirable side reactions emerging from amine radi-
Lewis acids[3] or Lewis bases,[4] transition metals[5] and cal cation intermediates, our preliminary investigation
fluoride ions.[6] Heteroatom-centered nucleophiles, was carried out on N-tosylaziridines (Table 1). First
such as chiefly alcohols, azides and halides have been we began with the ring-opening reactions in polar
devised for ring-opening addition of aziridines, and protic solvents, such as MeOH. When N-tosylaziridine
are of important interest because they provide a prac- 1a was treated with MeOH in the presence of 2 equiv.
tical synthetic access to 1,2-bifunctional compounds Na2S2O8, as an effective oxidative quencher,[11] and
containing amino ether, azido amine and b-halide 5 mol% RuACHTUNRTGENUNG(bpy)3Cl2 under the irradiation of blue
amine functionalities, and the resulting compounds LED, we observed the corresponding ring-opening
are found to be synthetically valuable in fundamental- product – the 1,2-amino ether 2a. The ring-opening
ly important transformations.[7] However, when an reaction of 1a with MeOH via visible-light photore-
aziridine is unsymmetrically substituted, two regioiso- dox catalysis was found to be highly regioselective
meric ring-opening products would be achieved and only the regioisomer derived from opening at the
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Table 1. Visible light-induced ring-opening of 1a.[a]
Entry
Additives
X
Time [h]
Yield[b] [%]
1
2
3
MeOH
OMe
Br
N3
1
3
5
2a, 86
3a, 86 (87:13)
4a, 90 (78:22)
LiBr, Hantzsch ester,[c] DMF
NaN3, Hantzsch ester,[c] DMF
[a]
Reaction conditions: aziridine 1a (0.1 mmol), Na2S2O8 (2 equiv.), Ru
ACHTUNGTRENNUNG
radiated under 1W blue LED at room temperature.
Isolated yield; the proportion of isomers given in parentheses was determined by H NMR spectroscopy.
Hantzsch ester=diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate.
[b]
[c]
1
substituted carbon atom was observed. In this reac- sponding products in moderate to good yields
tion, MeOH that served as a nucleophile could also (Table 2, entries 11 and 12). With respect to the regio-
be the hydrogen donor. Next, we examined other nu- selectivity observed in the reaction, we speculated
cleophiles and chose aprotic solvents instead of that such a result might depend on the electronic
MeOH. After a solvent and nucleophile screening, we effect (for instance, in the ring-opening of 2-arylaziri-
found that when 1a was reacted with 2 equiv. LiBr, dines) based upon the above results and the previous
1.1 equiv. Hantzsch ester, 2 equiv. Na2S2O8 and work from other groups,[1c] although most nucleo-
5 mol% RuACHTUNGTRENNUNG(bpy)3Cl2 in DMF under the irradiation of philes preferentially direct their attack to the site of
blue LED, 2-bromo-2-phenylethanamine 3a and 2- lower substitution.
bromo-1-phenylethanamine were obtained in 86%
The scope of the protective groups on the amine
yield with a ratio of 87:13. Under the same conditions, was examined by treatment of aziridines 1a’, 1a’’ and
when LiBr was replaced by NaN3, 2-azido-2-phenyl- 1a’’’ under the same conditions. In comparison with
ACHTUNGTRENNUNGethanamine 4a and 2-azido-1-phenylethanamine were the N-tosylaziridine, the reactions of the above three
obtained in 90% yield with a ratio of 78:22. The re- compounds were performed with lower efficiency. For
sults listed in Table 1 indicated the high regioselectivi- example, except of 2-methoxy-1-amine 2a’, neither
ty of this protocol. Notably, for the reactions in aprot- the 2-bromo- nor the 2-azido-1-amine compound has
ic solvents, for example, DMF, the Hantzsch ester was been obtained in the reaction [Scheme 2, Eq. (1)]. In
required to act as the hydrogen donor.[12] Further- the cases ofÀ1a’’ and 1a’’’, only the nucleophilic addi-
more, control experiments revealed that light and tion with N3 was effective and led to 2-azido-1-amine
photocatalyst were both necessary for productive re- compounds [Scheme 2, Eqs. (2) and (3)] in 82% and
activity.
To demonstrate the general value of this strategy,
67% yield respectively.
The reaction was also extended to the ring-opening
a number of aziridines was prepared and submitted to of chiral aziridine (S)-1a. To our great pleasure, treat-
the reaction conditions, and the results are summar- ment of (S)-1a in MeOH led to an optically pure
ized in Table 2. In all cases, the desired products were amino ether 2aa in 87% ee (Table 3, entry 1). Such
obtained in good yields with high regioselectivities. a result indicated an SN2-type nucleophilic addition to
The phenyl groups substituted with electron-donating the aziridine ring. Thus, we envisaged that a straight-
or electron-withdrawing groups did not affect the effi- forward approach to the enantioselective synthesis of
ciency and the regioselectivity of the reactions 1,2-amino esters could be achieved by performing the
(Table 2, entries 1–5). When the aromatic group was reaction in various alcohols via visible-light photore-
replaced by an alkyl one, the 2-amine compound was dox catalysis.[13] To demonstrate the general value of
preferentially formed through terminal nucleophilic this strategy, an array of alcohols was investigated,
addition at the less hindered position (Table 2, en- and the results are summarized in Table 3. With less
tries 6 and 13). Moreover, the reaction was not limit- hindered alcohols, such as primary, allylic and propar-
ed to terminal aziridines, multisubstituted aziridines gylic alcohols, the corresponding products were ob-
were also suitable substrates (Table 2, entries 7–10). tained in good yields with high ee (Table 3, entries 1–
Especially, for the aziridine 1i, we achieved the ring 3). A secondary alcohols (i-PrOH) was found to be
opened product at the dimethyl-substituted carbon, less reactive and a reduced yield was observed
which is mainly attributed to the stability of the car- (Table 3, entry 4). Under similar reaction conditions,
bocation. Cyclic N-tosylaziridines were also tolerated the more sterically crowded tert-butyl alcohol failed
under the reaction conditions to afford the corre- to give any ring-opening product.
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Regioselective Ring-Opening Nucleophilic Addition of Aziridines
Table 2. Visible light-induced ring-opening of aziridines.[a]
Entry
Substrates
Products
Time [h]
Yield[b] [%]
1
2
3
4
5
1a
1b
1c
1d
1e
Ar=Ph
2a
3a
4a
2b
3b
4b
2c
3c
4c
2d
3d
4d
2e
3e
4e
X=OMe
X=Br
X=N3
X=OMe
X=Br
X=N3
X=OMe
X=Br
X=N3
X=OMe
X=Br
X=N3
1
3
5
1
3
5
1
3
5
1
3
5
1
3
5
86
86 (87:13)
90 (78:22)
87
74 (82:18)
90 (72:28)
62
65 (87:13)
72 (83:17)
74
78 (80:20)
80 (73:27)
90
Ar=4-MeOC6H4
Ar=4-FC6H4
Ar=3-MeOC6H4
Ar=2-ClC6H4
X=OMe
X=Br
X=N3
85 (83:17)
72 (86:14)
6
7
1f
1g
2f
4 f
X=OMe
X=N3
5
7
60
82
2g
3g
4g
X=OMe
X=Br
X=N3
3
5
5
76
71
68
8
1h
1i
2h
2i
5
83
73
9
10
10
1j
2j
3j
X=OMe
X=Br
5
12
90
57
11
12
1k
2k
4k
X=OMe
X=N3
12
12
32
25
1l
2l
3l
4l
X=OMe
X=Br
X=N3
5
12
7
78
85
88
13
1m
4m
3
71
[a]
Reaction conditions: aziridine 1 (0.1 mmol), Na2S2O8 (2 equiv.), RuACHTUNGTREN(UNNG bpy)3Cl2 (5 mol%), additives and solvent (1 mL), irra-
diated under blue LED at room temperature.
Isolated yield; the proportion of isomers given in parentheses was determined by H NMR spectroscopy.
[b]
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Scheme 4. Proposed mechanism.
Scheme 2. Ring-opening reactions of aziridines with differ-
ent amine protecting groups.
catalyzed [3+2]alkyne/azide cycloaddition reaction to
give compound 7a in 70% yield.
The synthetic utility of the ring-opening products
Based upon the above results, a reaction mecha-
was exemplified by further transformations. Chemical nism was proposed as shown in Scheme 4. Under the
modification of the azide functionality was studied irradiation of visible light, Ru(II) was converted to its
using 4a as the substrate (Scheme 3). Azido amine excited-state Ru(II)*, which was then oxidatively
2À
2À
was easily converted to diamine 5a by hydrogenation. quenched by S2O8 to afford SO4 and Ru
Benzotriazole was readily obtained by the reaction of spectively. Sequential single-electron transfer from
in situ generated benzyne with 6a in 73% yield. Final- aziridine to Ru(III) served to form the amino radical
ACHTUNGTRENN(UNG III), re-
AHCTUNGTRENNUNG
ly, as expected, 4a was a suitable substrate for a Cu- cation intermediate I and regenerate catalyst Ru(II).
Concerted ring-opening and nucleophilic addition af-
forded amino radical intermediate II, which was con-
verted to the final product after abstraction of one hy-
drogen atom from MeOH or Hantzsch ester.
To add more credence of the existence of amino
radical intermediate II, a control experiment was car-
ried out with the addition of methyl vinyl ketone
(MVK) as the radical scavenger. As expected, the Mi-
chael radical addition product 8a was successfully ob-
tained (Scheme 5).
Table 3. Visible light-induced regioselective nucleophilic
ring-opening of (S)-1a with alclhols.[a]
Entry
R
Time [h]
Yield[b] [%]
ee[c] [%]
1
2
3
4
Me
allyl
propargyl
i-Pr
2
3
2
4
2aa, 86
2ab, 78
2ac, 94
2ad, 75
87
83
67
76
[a]
In all the cases the alcohol served as the solvent.
Isolated yield.
Determined by chiral HPLC.
[b]
[c]
Scheme 5. Control experiment by reaction of 1a with MVK.
Scheme 3. Transformation of the azide functionality in 4a.
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Sweeney, Synlett 1994, 145–147; c) M. Meguro, N.
Asao, Y. Yamamoto, Tetrahedron Lett. 1994, 35, 7395–
7398; d) W.-H. Leung, M. T. Yu, M. C. Wu, L.-L.
Yeung, Tetrahedron Lett. 1996, 37, 891–892; e) Z. Li,
M. Fernandez, E. N. Jacobsen, Org. Lett. 1999, 1, 1611–
1613; f) G. Sekar, V. K. Singh, J. Org. Chem. 1999, 64,
2537–2539; g) M. Chandrasekhar, G. Sekar, V. K.
Singh, Tetrahedron Lett. 2000, 41, 4677–4679; h) M.
Chandrasekhar, G. Sekar, V. K. Singh, Tetrahedron
Lett. 2000, 41, 10079–10083; i) G. Sabitha, S. Babu, M.
Rajkumar, C. S. Reddy, J. S. Yadav, Tetrahedron Lett.
2001, 42, 3955–3958; j) J. S. Yadav, B. V. S. Reddy,
G. M. Kumar, Synlett 2001, 1417–1418; k) T. Mita, I.
Fujimori, R. Wada, J. Wen, M. Kanai, M. Shibasaki, J.
Am. Chem. Soc. 2005, 127, 11252–11253; l) Y. Fukuta,
T. Mita, N. Fukuda, M. Kanai, M. Shibasaki, J. Am.
Chem. Soc. 2006, 128, 6312–6313; m) I. Fujimori, T.
Mita, K. Maki, M. Shiro, A. Sato, S. Furusho, M.
Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128,
16438–16439; n) R. Yu, Y. Yamashita, S. Kobayashi,
Adv. Synth. Catal. 2009, 351, 147–152; o) B. Wu, J. C.
Gallucci, J. R. Parquette, T. V. RajanBabu, Angew.
Chem. 2009, 121, 1146–1149; Angew. Chem. Int. Ed.
2009, 48, 1126–1129; p) Y. Hayashi, T. Kumamoto, M.
Kawahata, K. Yamaguchi, T. Ishikawa, Tetrahedron
2010, 66, 3836–3841.
In conclusion, we have developed a mild and effi-
cient protocol for the regioselective ring-opening nu-
cleophilic addition of the N-tosylaziridines via visible
light-induced photoredox catalysis. Moreover, the
enantioselective sythesis of 1,2-amino esters also
could be realized by an SN2-type ring-opening reac-
tion of optically pure aziridine with alcohols. Finally,
further experiments provided a clear understanding of
the reaction mechanism. Ongoing studies are focused
on applying this reaction to more complex molecules.
Experimental Section
General Procedure
A 10-mL round-bottom flask was equipped with a magnetic
stir bar and was charged with aziridine (0.1 mmol), Na2S2O8
(47.6 mg, 0.2 mmol), RuACHTNUTRGNEUNG(bpy)3Cl2 (3.8 mg, 5 mmol), additives
(LiBr or NaN3, 2 equiv.; Hantzsch ester, 1.1 equiv.) and sol-
vent (1 mL). The round-bottom flask was placed under blue
LED irradiation and the mixture allowed to stir at room
temperature for 1–12 h. Reaction progress was checked by
thin layer chromatography (TLC). The reaction mixture was
concentrated under vacuum, and ring opening products
were purified by flash column chromatography.
[4] a) S. Minakata, Y. Okada, Y. Oderaotoshi, M. Komat-
su, Org. Lett. 2005, 7, 3509–3512; b) J. Wu, X. Sun, H.-
G. Xia, Eur. J. Org. Chem. 2005, 22, 4769–4772; c) J.
Wu, X. Sun, Y. Shengqing, W. Sun, Tetrahedron Lett.
2006, 47, 4813–4816; d) J. Wu, X. Sun, W. Sun, Org.
Biomol. Chem. 2006, 4, 4231–4234; e) S. Matsukawa, K.
Tsukamoto, Org. Biomol. Chem. 2009, 7, 3792–3796;
f) S. Matsukawa, T. Harada, S. Yasuda, Org. Biomol.
Chem. 2012, 10, 4886–4890.
[5] a) M. Bera, S. Roy, J. Org. Chem. 2010, 75, 4402–4412;
b) M. Bera, S. Pratihar, S. Roy, J. Org. Chem. 2011, 76,
1475–1478; c) C.-Y. Huang, A. G. Doyle, J. Am. Chem.
Soc. 2012, 134, 9541–9544; d) D. K. Nielsen, C.-Y.
Huang, A. G. Doyle, J. Am. Chem. Soc. 2013, 135,
13605–13609; e) M. L. Duda, F. E. Michael, J. Am.
Chem. Soc. 2013, 135, 18347–18349.
Acknowledgements
We are grateful for the financial supports from China NSFC
(Nos. 21272047 and 21372055), SKLUWRE (No. 2012DX10)
and the Fundamental Research Funds for the Central Univer-
sities (Grant No. HIT.BRETIV.201310).
References
[1] For reviews on aziridine chemistry, see: a) A. Padwa,
A. D. Woodhouse, in: Comprehensive Heterocyclic
Chemistry, 1ednst ednVol. 7, (Eds.: A. R. Katrizky,
C. W. Rees), Pergamon, New York, 1984, pp 47–93;
b) D. Tanner, Angew. Chem. 1994, 106, 625–646;
Angew. Chem. Int. Ed. Engl. 1994, 33, 599–619; c) J. B.
Sweeny, Chem. Soc. Rev. 2002, 31, 247–258.
[2] For recent reviews on ring-opening reactions of aziri-
dines, see: a) X. E. Hu, Tetrahedron 2004, 60, 2701–
2743; b) V. V. Fokin, P. Wu, in: Aziridine and Epoxide
in Organc Synthesis, (Ed.: A. K. Yudin), Wiley-VCH,
Weinheim 2006, chapter 12, pp 443–475; c) I. D. G.
Watson, L. Yu, A. K. Yudin, Acc. Chem. Res. 2006, 39,
194–206; d) G. S. Singh, M. D’hooghe, N. D. Kimpe,
Chem. Rev. 2007, 107, 2080–2135; e) C. Schneider,
Angew. Chem. 2009, 121, 2116–2118; Angew. Chem.
Int. Ed. 2009, 48, 2082–2084; f) P. Lu, Tetrahedron 2010,
[6] J. Wu, X.-L. Hou, L.-X. Dai, J. Org. Chem. 2000, 65,
1344–1348.
[7] a) A. R. Khokhar, A. B. Salaam, T. Brown, P. S.
Roman, J. Med. Chem. 1991, 34, 325–329; b) D. J. Ager,
I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835–875.
[8] a) G.-L. Zhao, C. Yang, L. Guo, H.-N. Sun, C. Chen,
W.-J. Xia, Chem. Commun. 2012, 48, 2337–2339; b) G.-
L. Zhao, C. Yang, L. Guo, H.-N. Sun, R. Lin, W.-J. Xia,
J. Org. Chem. 2012, 77, 6302–6306; c) H.-N. Sun, C.
Yang, F. Gao, Z. Li, W.-J. Xia, Org. Lett. 2013, 15, 624–
627; d) L. Guo, C. Yang, L.-W. Zheng, W.-J. Xia, Org.
Biomol. Chem. 2013, 11, 5787–5792; e) Y.-T. Zhao, Z.
Li, C. Yang, R. Lin, W.-J. Xia, Beilstein J. Org. Chem.
2014, 10, 622–627.
[9] For some reviews of photoredox catalysis, see: a) T. P.
Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527–
532; b) A. Inagaki, M. Akita, Coord. Chem. Rev. 2010,
254, 1220–1239; c) J. M. R. Narayanam, C. R. J. Ste-
phenson, Chem. Soc. Rev. 2011, 40, 102–113; d) J.
Xuan, W.-J. Xiao, Angew. Chem. 2012, 124, 6934–6944;
´
66, 2549–2560; g) S. Stankovic, M. D’hooghe, S. Catak,
H. Eum, M. Waroquier, V. V. Speybroeck, N. De
Kimpe, H. J. Ha, Chem. Soc. Rev. 2012, 41, 643–665.
[3] a) S. Matsubara, T. Kodama, K. Utimoto, Tetrahedron
Lett. 1990, 31, 6379–6380; b) H. M. I. Osborn, J. B.
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢁ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
5
ÞÞ
These are not the final page numbers!

COMMUNICATIONS
Hongnan Sun et al.
Angew. Chem. Int. Ed. 2012, 51, 6828–6838; e) L. Shi,
W.-J. Xia, Chem. Soc. Rev. 2012, 41, 7687–7697; f) C. K.
Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev.
2013, 113, 5322–5363.
2013, 135, 1823–1829; h) J. Xuan, X.-D. Xia, T.-T. Zeng,
Z.-J. Feng, J.-R. Chen, L.-Q. Lu, W.-J. Xiao, Angew.
Chem. 2014, 126, 5759–5762; Angew. Chem. Int. Ed.
2014, 53, 5653–5656.
[10] Selected examples for visible light-induced amino radi-
cal cation: a) A. G. Condie, J. C. Gonzꢂlez-Gꢃmez,
C. R. J. Stephenson, J. Am. Chem. Soc. 2010, 132, 1464–
1465; b) M. Rueping, D. Leonori, T. Poisson, Chem.
Commun. 2011, 47, 9615–9617; c) M. Chen, Z.-T.
Huang, Q.-Y. Zheng, Chem. Commun. 2012, 48, 11686–
11688; d) S. Zhu, M. Rueping, Chem. Commun. 2012,
48, 11960–11962; e) Y. Miyake, K. Nakajima, Y. Nishi-
bayashi, Chem. Commun. 2013, 49, 7854–7856; f) J.
Xie, Q. Xue, H. Jin, H. Li, Y. Cheng, C. Zhu, Chem.
Sci. 2013, 4, 1281–1286; g) S. Zhu, A. Das, L. Bui, H.
Zhou, D. P. Curran, M. Rueping, J. Am. Chem. Soc.
[11] a) H. S. White, A. J. Bard, J. Am. Chem. Soc. 1982, 104,
6891–6895; b) U. Nickel, Y.-H. Chen, S. Schneider,
M. I. Silva, H. D. Burrows, S. J. Formosinho, J. Phys.
Chem. 1994, 98, 2883–2888; c) D. A. Fancy, T. Kodadek,
Proc. Natl. Acad. Sci. USA 1999, 96, 6020–6024; d) C.-
H. Dai, F. Meschini, J. M. R. Narayanam, C. R. J. Ste-
phenson, J. Org. Chem. 2012, 77, 4425–4431.
[12] J. D. Nguyen, E. M. D’Amato, J. M. R. Narayanam,
C. R. J. Stephenson, Nat. Chem. 2012, 4, 854–859.
[13] a) M. K. Ghorai, K. Das, D. Shukla, J. Org. Chem.
2007, 72, 5859–5862; b) M. K. Ghorai, D. Shukla, A.
Bhattcharyya, J. Org. Chem. 2012, 77, 3740–3753.
6
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Adv. Synth. Catal. 0000, 000, 0 – 0
ꢁ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
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These are not the final page numbers!