Domino Radical Addition/Oxidation Sequence with Photocatalysis: One-Pot Synthesis of Polysubstituted Furans from α-Chloro-Alkyl Ketones and Styrenes

Article abstract of DOI:10.1002/chem.201602053

A new domino reaction has been developed that allows the combination of styrenes and α-alkyl ketone radicals to afford a wide array of polysubstituted furans in good to excellent yields under mild and simple reaction conditions. The key to success of this novel protocol is the use of photocatalyst fac-Ir(ppy)₃and oxidant K₂S₂O₈. Mechanistic studies by a radical scavenger and photoluminescence quenching suggest that a radical addition/oxidation pathway is operable.

Full text of DOI:10.1002/chem.201602053

A Journal of
Accepted Article
Title: Domino Radical Addition/Oxidation Sequence via Photocatalysis: One-Pot
Synthesis of Polysubstituted Furans from α-Chloro-Alkyl Ketones and Styre-
nes
Authors: Qiang Liu; Shuang Wang; Wen-Liang Jia; Lin Wang; Li-Zhu Wu
This manuscript has been accepted after peer review and the authors have elected
to post their Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by using the Digital
Object Identifier (DOI) given below. The VoR will be published online in Early View as
soon as possible and may be different to this Accepted Article as a result of editing.
Readers should obtain the VoR from the journal website shown below when it is pu-
blished to ensure accuracy of information. The authors are responsible for the content
of this Accepted Article.
To be cited as: Chem. Eur. J. 10.1002/chem.201602053
Link to VoR: http://dx.doi.org/10.1002/chem.201602053
Supported by

Chemistry - A European Journal
10.1002/chem.201602053
COMMUNICATION
Domino Radical Addition/Oxidation Sequence via Photocatalysis:
One-Pot Synthesis of Polysubstituted Furans from α-Chloro-Alkyl
Ketones and Styrenes
Shuang Wang,[a] Wen-Liang Jia, [a] Lin Wang,[a] Qiang Liu*[a] and Li-Zhu Wu* [b]
Abstract: A new domino reaction has been developed that allows
the combination of styrenes and α-alkyl ketone radicals to afford a
wide array of polysubstituted furans in good to excellent yields under
mild and simple reaction condition. Key to the success of this novel
protocol is the use of photocatalyst fac-Ir(ppy)3 and oxidant K2S2O8.
Mechanistic studies by radical scavenger and photoluminescence
quenching suggest that a radical addition/oxidation pathway is
operable.
aryl ketones with α,β-unsaturated carboxylic acids, a protocol
that would produce α-aryl ketone radical for constructing a
variety of
targeted molecules (Scheme 1a). Later on,
Antonchick et al.[10] also reported copper-catalyzed radical
addition of acetopheones to alkynes and obtained a series of
multisubstituted furans, a strategy which also offers α-aryl
ketone radical (Scheme 1b). However, all these systems require
either high loading of transition-metal catalysts or radical
initiators and high temperature.[11]
Five-membered heterocycle furans, as fundamental structural
units, broadly exist in many bioactive natural products and
diverse pharmaceuticals[1] such as furan-2-carbohydrazide and
PTTP,[2] which are used as antagonists treating diseases like
diabetes and Parkinson. Besides, furan units can be used as
versatile synthetic intermediates in the synthesis of complex
natural products.[3] For example, double bonds of furans could
be utilized in pericyclic reaction and Diels-Alder addition; enol
structure could be applied in Michael-type addition.
Consequently, the development of efficient methods for the
synthesis of multisubstituted furans has gained much attention.
Over the past few decades, there are some commonly
approaches to polysubstituted furan derivatives such as
classical
methods
of
Paal-Knorr/Feist-Benary
cyclocondensation[4] and conventional means of metal-mediated
cycloisomerization.[5] however, these protocols often suffer from
limited availability of functionalized precursors and harsh
conditions. Therefore, the development of more efficient and
practical strategies to prepare polysubstituted furan derivatives
from simple and readily accessible raw materials is still highly
sought after.
Over the past century, free-radical chemistry has grown at a
dramatic pace within the field of organic chemistry. Among the
vast radical libraries, α-ketone radicals are potentially promising
intermediates for various transformations such as cyclization,[6]
oxidation[7] and addition,[8] which could successfully introduce
heteroatom oxygen into compounds. In the recent years, α-aryl
ketone radicals, as representative cases of α-ketone radicals,
are widely applied to synthesize polysubstituted furans due to
the polarity of carbonyl group. For example, in 2013, Zhang and
his workers[9] described a novel method for the generation of
polysubstituted furans via copper-mediated annulation of simple
Scheme 1. Preparation of polysubstituted furans
Recently, visible-light photocatalysis has offered an
economical and environmentally benign platform for the
development of free radical reaction. Especially, reductive
dehalogenation of electron-deficient haloalkanes has become an
efficient and attractive strategy for producing free radicals
through photoinitiated single-electron transfer (SET) pathways,
due to the ingenious research efforts of some groups, such as
MacMillan,[12] Stephenson,[13] Gagne’,[14] Yu,[15] and Xiao.[16] By
far, our laboratory has also successfully synthesized γ-
Lactones,[17] difluoromethylenephosphonyl (DFMP)-substituted
[a]
[b]
Shuang Wang, Wen-Liang Jia, Prof. Dr. Qiang Liu
State Key Laboratory of Applied Organic Chemistry, College of
Chemistry and Chemical Engineering,
Lanzhou University, Lanzhou 730000 (P. R. China.)
E-mail: liuqiang@lzu.edu.cn
aromatic
compounds[18]
and
6-(DFMP)-substituted
Prof. Dr. L.-Z. Wu
phenanthridines[19] by the method of reductive dehalogenation
via visible-light photoredox catalysis. Recently, Yu’s group[20]
has reported a novel method for generating polysubstituted
furans using a photoredox neutral coulping of alkynes with 2-
bromo-1,3-dicarbonyl compounds (Scheme 1c). However,
Key Laboratory of Photochemical Conversion and
Optoelectronic Materials, Technical Institute of Physics and
Chemistry & University of Chinese Academy of Sciences, the
Chinese Academy of Sciences
Supporting information for this article is given via a link at the end of
the document.((Please delete this text if not appropriate))

Chemistry - A European Journal
10.1002/chem.201602053
COMMUNICATION
Table 1 Optimization of reaction conditions [a]
We initially launched our study by using styrene 1a (1.0
equiv.), 2-chloro-1-phenylpropan-1-one 2a (2.0 equiv.) and 2
mol% of fac-Ir(ppy)3 in dry CH3CN. It was encouraging to see
that the desired product 3a was obtained in 21% yield after 24 h
of irradiation (blue LEDs, λ = 450 nm) at room temperature when
using Na2S2O8 (2.0 equiv.) as the oxidant and Cs2CO3 (2.0
equiv.) as the base (Table 1, entry 1). Based on the properties of
the substrates, the solvent was changed to several other polar
aprotic solvents such as acetone, DMSO, DMF and CH2Cl2
(Table 1, entries 2-5), and then DMSO was chosen as the ideal
organic solvent for the reaction. With the best solvent in hand,
other different bases including K3PO4, KOAc, K2CO3, 2,6-lutidine
and DBN were tested (Table 1, entries 6-10), we were delighted
to see that the yield of 3a was greatly improved to 71% in the
presence of 2,6-lutidine. Furthermore, some kinds of oxidants
containing K2S2O8, TBHP and DCP were used in this reaction to
replace Na2S2O8 (Table 1, entries 11-14), and the yield was
further increased to 84% when using K2S2O8 as the ideal oxidant.
Entry
1
catalyst
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
fac-Ir(ppy)3
eosin Y
Base[b]
Cs2CO3
Oxidant[c]
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
Na2S2O8
K2S2O8
(NH4)2S2O8
TBHP
Solvent[d]
CH3CN
acetone
DMF
Yield (%)[e]
21
2
Cs2CO3
16
3
Cs2CO3
24
4
Cs2CO3
DMSO
CH2Cl2
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
51
5
Cs2CO3
27
6
K3PO4
53
7
KOAc
48
Table 2. Scope of arylethenes/ heteroarylethenes[a, b]
8
K2CO3
56
9
2,6-lutidine
DBN
71
blue LEDs
fac-Ir(ppy)3 (2 mol%)
O
10
11
12
13
14
15
16f
17
18
19g
20
45
X
R
+
O
2,6-lutidine
2,6-lutidine
2,6-lutidine
2,6-lutidine
2,6-lutidine
2,6-lutidine
2,6-lutidine
2,6-lutidine
2,6-lutidine
2,6-lutidine
84
X
R
K2S2O8 (2.0 equiv.)
2,6-lutidine (2.0 equiv.)
DMSO, rt, 24h
Cl
1a
2
3
55
36
DCP
77
——
51
K2S2O8
K2S2O8
K2S2O8
K2S2O8
K2S2O8
23
N.R.
N.R.
N.R.
N.R.
Ru(bpy)3Cl2
fac-Ir(ppy)3
——
[a] Reaction conditions: a mixture of 1a (0.2 mmol, 1.0 equiv.), 2 (0.4 mmol,
2.0 equiv.), base (0.4 mmol, 2.0 equiv.), oxidant (0.4 mmol, 2.0 equiv.) and
photocatalyst (0.004 mmol, 2.0 mol%) in dry solvent (2.0 mL) was irradiated
with a 3 W blue LEDs at room temperature for 24 h. The reaction was
conducted in
diazabicyclo[4.3.0]non-5-ene. [c] TBHP = tert-butyl hydroperoxide; DCP =
dicumyl peroxide. [d] DMF N,N-dimethylformamide; DMSO
a
sealed tube full of Ar gas. [b] DBN
=
1,5-
=
=
dimethylsulfoxide; [e] Isolated yield, N.R. = No Reaction. [f] Exposed in the air.
[e] Isolated yield. [g] No irradiation.
when α-bromo-aryl ketones are employed, the products are
naphthols instead of polysubstituted furans. Taking inspiration
from our previously developed photoredox reductive
dehalogenation,[17-19] we recently hypothesized that α-aryl ketone
radical could be achieved under much milder conditions from
commercially available α-chloro-aryl ketones via visible-light
photoredox catalysis and that polysubstituted furans could be
achieved by combination of α-chloro-aryl ketones and styrenes
via a radical addition/oxidation pathway, a novel method we
presented in this study could offer the targeted compounds in
just one step(Scheme 1d).
[a] Reaction conditions: a mixture of 1 (0.4 mmol, 2.0 equiv.), 2a (0.2 mmol,
1.0 equiv.), K2S2O8 (0.4 mmol, 2.0 equiv.), 2,6-Lutidine (0.4 mmol, 2.0 equiv.)
and fac-Ir(ppy)3 (0.004 mmol, 2.0 mol%) in dry DMSO (2.0 ml) was irradiated
with a 3 W blue LED lamp at room temperature for 24h. [b] Isolated yield.

Chemistry - A European Journal
10.1002/chem.201602053
COMMUNICATION
To identify the necessity of K2S2O8, the reaction was carried out
in the absence of oxidant (Table 1, entry 15), and only 51% yield
of 3a was obtained. When the reaction was exposed in the air,
the yield of the desired product decreased dramatically (Table 1,
entry 16). Moreover, the reaction failed in other photocatalysts
suitable substrates, as detailed in table 3. It was noteworthy that
electron-donating and -withdrawing substituents had little
influence on the reaction efficiencies and corresponding α-
chloro-aryl ketones were excellent substrates for these reactions
(Table 3, 4a-b and 4d-f, 65-80%). Notably, α-chloro-aryl ketone
such as eosin Y and Ru(bpy)3Cl2 (Table 1, entries 17-18). Finally, bearing a long aliphatic side chain on the α-position offered a
control experiments showed that no desired products were
detected in the absence of light or fac-Ir(ppy)3 (Table 1, entries
19-20), indicating that the reaction was a visible-light-driven
photoredox system.
desired yield (Table 3, 4b, 80%). Not surprisingly, α-chloro-aryl
ketone bearing a bulk aryl ring was also tolerated under the
standard condition (Table 3, 4c, 35%), albeit the yield is not
desirable, presumably owing to the steric hindrance around the
site of radical generation.
Under the optimal conditions, we next investigated the
arylethenes scope of this novel and visible-light-driven
transformation, as revealed in table 2. A vast variety of
substituted arylethenes/heteroarylethenes, including electron-
withdrawing and electron-donating groups, could successfully
react with 2-chloro-1-phenylpropan-1-one 1, generating the
corresponding products in good to moderate yields (Table 2, 3a-
n, 34-86%). Nevertheless, substrates bearing electron-donating
and weak electron-withdrawing substituents (Table 2, 3a-f, 3h
and 3j-k, 73-86%) such as methyl, methoxyl, fluoro, and chloro
delivered relatively higher yields than those with strong electron-
withdrawing groups (Table 2, 3l-m, 40-50%) such as
trifluoromethyl and cyano. On the other hand, sterically
demanding substrate (Table 2, 3g, 35%) had obvious influence
on yield. Moreover, the position of substituents on the aryl ring
(Table 2, 3h-i, 57-73%) had certain effect on the yield and the
yields for chloro substituted products followed the order of
meta<para. Finally, when heteroarylethene was employed as a
substrate (Table 2, 3n, 34%), the product yield was slightly
affected, a result attributed to the stability of the pyridine ring in
the reaction condition.
In order to investigate the mechanism of this transformation,
we performed a series of experiments (Scheme 2). When radical
inhibitor TEMPO was introduced into the photocatalytic system,
no desired product was detected. To our delight, the adduct of
the radical inhibitor with 2-chloro-1-phenylpropan-1-one was
detected by ESI-HRMS, thus providing plausible evidence of α-
aryl ketone radical formation. In addition to the trapping
investigation, from the UV-Vis absorption spectra, we can note
that only the photocatalyst fac-Ir(ppy)3 can be excited under the
irradiation of blue LEDs (λ = 450 nm), while both 2-chloro-1-
phenylpropan-1-one and styrene are transparent to a photon of
blue light (see figure S1 in the Supporting Information). At the
same time, the photoluminescence of fac-Ir(ppy)3 was quenched
by 2-chloro-1-phenylpropan-1-one 1a with a rate constant of 1.3
x 103 L mol-1(Scheme 2, b). however, the quenching rate
constant of fac-Ir(ppy)3 with styrene 2a or K2S2O8 was smaller
(8.86 x 102 L mol-1 and 1.4 x 102 L mol-1). The oxidation potential
of the excited fac-Ir(ppy)3 is -1.73 V (vs. SCE) [21], which is much
lower than the reduction potential of 2-chloro-1-phenylpropan-1-
one (-1.48 V, vs. Ag/Ag+, 0.1 M) [22]. Therefore, the significant
emission quenching of fac-Ir(ppy)3 by 1a should be attributed to
the electron transfer from the excited photocatalyst to 1a. This
finding indicates that the electron transfer from the excited fac-
Ir(ppy)3 to 1a is favourable.
Table 3. Scope of α-chloro arylketones[a, b]
R2
O
blue LEDs
fac-Ir(ppy)3 (2 mol%)
R2
+
a)
R1
TEMPO (2.0 equiv.)
O
O
Cl
O
R1
K2S2O8 (2.0 equiv.)
2,6-lutidine (2.0 equiv.)
DMSO, rt, 24h
fac-Ir(ppy)3 (2 mol%)
4
O
+
2a
1
N
Cl
2,6-lutidine (2.0 equiv.), DMSO
3W 450 nm LEDs, rt
[M+H]+ 290.2115
b)
3.0
1a
2a
K2S2O8
2.5
2.0
1.5
1.0
0.0
0.2
0.4
0.6
0.8
1.0
1.2
1.4
Concentration (mM)
a Reaction conditions: a mixture of 1a (0.4 mmol, 2.0 equiv.), 2 (0.2 mmol, 1.0
equiv.), K2S2O8 (0.4 mmol, 2.0 equiv.), 2,6-Lutidine (0.4 mmol, 2.0 equiv.) and
fac-Ir(ppy)3 (0.004 mmol, 2.0 mol%) in dry DMSO (2.0 ml) was irradiated with
a 3 W blue LED lamp at room temperature for 24h. b Isolated yield.
Scheme 2. Mechanism investigation (b: Stern-Volmer plots of fluorescence
quenching of fac-Ir(ppy)3 by 1a, 2a and K2S2O8)
Based on the above experimental results and previous
reports[9, 23], a radical addition/oxidation pathway was proposed
in Scheme 3. SET from the excited photocatalyst to 1a
We then turned our attention to the scope of α-chloro-aryl
ketones that can participate in this new protocol and function as

Chemistry - A European Journal
10.1002/chem.201602053
COMMUNICATION
generates electron-deficient α-carbonyl carbon radical A along
with IrIV(ppy)3. Intermolecular π-addition of the radical A to
styrene 2a produces benzylic radical B. Further SET from
radical B (Eox1/2 = 0.73 V, vs. SCE) [21] to IrIV(ppy)3 (Ered1/2 = 0.77
V, vs. SCE)[24] gives carbocation C and regenerates the
photocatalyst. Subsequently, cyclization and deprotonation of C
aided by the base result in dihydrofuran derivative E. Finally,
oxidation of intermediate E by the excited photocatalyst or
K2S2O8 provides the desired product 3a.
Acknowledgements
We are grateful for financial support from the Ministry of
Science and Technology of China (2013CB834804), NSFC
(21572090 and 21172102), and the fundamental research funds
for the central universities (lzujbky-2015-49).
Keywords: domino reaction • polysubstituted furans • K2S2O8 •
room temperature • photocatalysis
[1] a) D. M. Donnelly, M. J. Meegan, In Comprehensive Heterocyclic
Chemistry; A. R. Katritzky, C. W. Rees, Eds.; Pergamon Press: Oxford,
1984; Vol.4, pp 705-709; b) X. L. Hou, Z. Yang, H. N. C. Wong,Progress
in Heterocyclic Chemistry, Vol. 15(Eds.: G. W. Gribble, T. L. Gilchrist),
Pergamon, Oxford, 2003, pp. 167–205; c) D. J. Mortensen, A. L.
Rodrı´guez, K. E. Carlson, J. Sun, B. S. Katzenellenbogen, J. A.
Katzenellenbogen, J. Med. Chem., 2001, 44, 3838-3848; d) O. Z. Ye, S. X.
Xie, M. Huang, W. J. Huang, J. P. Lu, Z. Q. Ma, J. Am. Chem. Soc., 2004,
126, 13940-13941.
[2] a) F. Hasegawa, K. Niidome, C. Migihashi, M. Murata, T. Negoro, T.
Matsumoto, K. Kato, A. Fujii, Bioorg. Med. Chem. Lett., 2014, 24, 4266-
4270; b) N. Kumari, C. B. Mishra, A. Prakash, N. b Kumar, R. Mongre, P.
M. Luthra, Neurosc. Lett., 2014, 558, 203-207.
[3] a) B. H. Lipshutz, Chem. Rev., 1986, 86, 795-819; b) M. Avalos, R.
Babiano, J. L. Bravo, P. Cintas, J. C. Palacios, Tetrahedron Lett., 1998,
39, 9301-9304; c) C. Tarducci, J. P. S. Badyal, S. A. Brewer, C. Willis,
Chem. Commun., 2005, 406–408;
[4] a) V. Amarnath, K. Amarnath, J. Org. Chem., 1995, 60, 301-307; b) X. -S.
Fan, Y. He, L. -Y. Cui, X. -Y. Zhang, J. -J. Wang, Green Chem., 2011, 13,
3218-3223; c) G. Mross, E. Holtz, P. Langer, J. Org. Chem., 2006, 71,
8045-8049.
Scheme 3. Proposed mechanism
In conclusion, we have developed a novel and straightforward
way to synthesis of polysubstituted furans through domino
reaction of inexpensive and commercial availably substrates α-
chloro-aryl ketones and arylethenes/ heteroarylethenes under
visible-light irradiation, a one-pot protocol which exhibits broad
scope and wide functional group tolerance. Furthermore, the
success of this strategy offered a solid framework for the further
development of our research programs in visible-light
photocatalysis. The further development of this synthetically
valuable photocatalytic processes is a continuing effort in our
laboratory.
[5] a) J. A. Marshall, E. D. Robinson, J. Org. Chem., 1990, 55, 3450-3451; b)
A. S. K. Hashmi, T. L. Ruppert, J. W. Bats, J. Org. Chem., 1997, 62,
7295-7304; c) S. -M. Ma, L. -H. Lu, J. -L. Zhang, J. Am. Chem. Soc., 2004,
126, 9645-9660; d) Y. Xia, Y. -M. Xia, R. Ge, Z. Liu, Q. Xiao, Y. Zhang, J.
-B. Wang, Angew. Chem. Int. Ed., 2014, 53, 3917-3921; e) T. -L. Yao, X. -
X. Zhang, R. C. Larock, J. Am. Chem. Soc., 2004, 126, 11164-11165; f) C.
-F. Lee, L. -M. Yang, T. -Y. Hwu, T. -Y. Luh, J. Am. Chem. Soc., 2000,
122, 4992-4993; g) X. Cui, X. Xu, L. Wojtas, M. M. Kim, X. P. Zhang, J.
Am. Chem. Soc., 2012, 134, 19981-19984.
[6] a) S. Ozaki, H. Matsshita, H. Ohmori, J. Chem. Soc., Chem. Commun.,
1992, 1120-1122; b) S. Ozaki, E. Matsui, J. Waku, H. Ohmori,
Tetrahedron Lett., 1997, 38, 2705-2708; c) H. Yorimitsu, T. Nakamura, H.
Shinokubo, K. Oshima, J. Org. Chem., 1998, 63, 8604-8605; d) E. Lee, C.
H. Yoon, T. H. Lee, J. Am. Chem. Soc., 1998, 120, 7469-7478; e) E.
Dunach, A. P. Esteves, A. M. Freitas, M. J. Medeiros, S. Olivero,
Tetrahedron Lett., 1999, 40, 8693-8696;
Experimental Section
[7] a) R. Braslau, J. R. Axon, B. Lee, Org. Lett., 2000, 2, 1399-1401.
[8] a) D. P. Curran, C. –T. Chang, Tetrahedron Lett., 1987, 28, 2477-2480; b)
K. Mizuno, M. Ikeda, S. Toda, Y. Otsuji, J. Am. Chem. Soc., 1988, 110,
1288-1290; c) J. L. Belletire, N. O. Mahmoodi, Tetrahedron Lett., 1989, 30,
4363-4366; d) H. Yorimitsu, K. Wakabayashi, H. Shinokubo, K. Oshima,
Tetrahedron Lett., 1999, 40, 519-522.
General procedure for the preparation of the products: In a 10 mL
snap cap vial equipped with a magnetic stirring bar and rubber septum,
the K2S2O8 (0.4 mmol), fac-Ir(ppy)3 (2 mol%), 2,6-lutidine (0.4 mmol), α-
chloro-propiophenones 1 (0.4 mmol) were dissolved in dry DMSO (2 mL).
The mixture was bubbled with a stream of argon for 30 min via a syringe
needle, then the styrenes 2 ( 0.2 mmol) was added into a snap cap vial
through a 100 μL microsyringe. The vial was then irradiated by using two
3W 450 nm blue LEDs. The process of the reaction was monitored by
thin-layer chromatography at regular intervals. After 24 hours, H2O (5.0
mL) was added into the reaction mixture. Then, the mixture was
extracted with Et2O and the combined organic layers were dried over
Na2SO4 and the solvent was removed under vacuum. The residue was
purified by silica gel column chromatography using petroleum/ ethyl
acetate to give the desired product.
[9] Y. -Z. Yang, J. -Z. Yao, Y. -H. Zhang, Org. Lett., 2013, 15, 3206-3209.
[10] S. Manna, A. P. Antonchick, Org. Lett., 2015, 17, 4300-4303.
[11] a) J. Iqbal, B. Bhatia, N. K. Nayyar, Chem. Rev., 1994, 94, 519-564; b) D.
Bebbington, J. Bentley, P. A. Nilsson, A. F. Parsons, Tetrahedron Lett.,
2000, 41, 8941-8945; c) J. M. Muñoz-Molina, T. R. Belderrain, P. J.
Pérez, Eur. J. Inorg. Chem., 2011, 21, 3155-3164; d) M. Tobisu, K. Koh,
T. Furukawa, N. Chatani, Angew.Chem. Int. Ed. 2012, 51, 11363-11366;
e) B. Zhang, A. Studer, Org. Lett. 2014, 16, 3990-3993.
[12] a) D. A. Nicewicz, D. W. C. MacMillan, Science, 2008, 322, 77-80; b) D.
A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc., 2009,
131, 10875-10877; c) H.-W. Shih, M. N. Vander Wal, R. L. Grange, D. W.

Chemistry - A European Journal
10.1002/chem.201602053
COMMUNICATION
C. MacMillan, J. Am. Chem. Soc., 2010, 132, 13600-13603.
[13] a) J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, J. Am. Chem.
Soc., 2009, 131, 8756-8757; b) J. D. Nguyen, J. W. Tucker, M. D.
Konieczynska, C. R. J. Stephenson, J. Am. Chem. Soc., 2011, 133,
4160–4163.
[20] H. Jiang, Y. -Z. Cheng, Y. Zhang, S. -Y. Yu, Org. Lett., 2013, 15, 4884-
4887.
[21] C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113,
5322-5363.
[22] D. D. Tanner, H. K. Singh, J. Org. Chem., 1986, 51, 5182-5186.
[23] a) Y. Koga, H. Kusama, K. Narasaka, Bull. Chem. Soc. Jpn., 1998, 71,
475-482; b) B. M. Casey, C. A. Eakin, J. -L. Jiao, D. V. Sadasivam, R. A.
Flowers, Tetrahedron, 2009, 65, 10762-10768; c)M. Ghosh, S. Mishra, A.
Hajra, J. Org. Chem., 2015, 80, 5364-5368; d) T. Naveen, R. Kancherla,
D. Maiti, Org. Lett., 2014, 16, 5446-5449; e) S. Ishikawa, Y. Noda, M.
Wada, T. Nishikata, J. Org. Chem., 2015, 80, 7555-7563; f) M. Ghosh, S.
Mishra, A. Hajra, Org. Biomol. Chem., 2015, 13, 309-314; g) S. Tang, K.
Liu, Y. Long, X. -T. Qi, Y. Lan, A. Lei, Chem. Commun., 2015, 51, 8769-
8772; h) R. -R. Liu, J. -J. Hong, C. -J. Lu, M. Xu, J. -R. Gao, Y. -X. Jia,
Org. Lett., 2015, 17, 3050-3053.
[14] a) R. S. Andrews, J. J. Becker, M. R. Gagne’, Angew. Chem., Int. Ed.,
2010, 49, 7274-7276; b) R. Andrews, J. J. Becker, M. R. Gagne’, Org.
Lett., 2011, 13, 2406-2409.
[15] a) H. Jiang, Y. -Z. Cheng, R. Z. Wang, M. -M. Zeng, Y. Zhang, S. Yu,
Angew. Chem. Int. Ed., 2013, 52, 13289-13292; b) X. -Y. Sun, S. Yu,
Org. Lett., 2014, 16, 2938-2941.
[16] Y. -Q. Zou, W. Guo, F. -L. Liu, L. -Q. Lu, J. -R. Chen, W. -J. Xiao, Green
Chem., 2014, 16, 3787-3795.
[17] X. -J. Wei, D. -T. Yang, L. Wang, T. Song, L. -Z. Wu, Q. Liu, Org. Lett.,
2013, 15, 6054-6057.
[18] L. Wang, X. -J. Wei, W. -L. Lei, H. Chen, L. -Z. Wu, Q. Liu, Chem.
Commun., 2014, 50, 15916-15919.
[24] D. D. M. Wayner, A. Houmam, Acta Chem. Sand., 1998, 52, 377-384.
[19] S. Wang, W. -L. Jia, L. Wang, Q. Liu, Eur. J. Org. Chem., 2015, 31, 6817-
6821.
[20] H. Jiang, Y. -Z. Cheng, Y. Zhang, S. -Y. Yu, Org. Lett., 2013, 15, 4884-
4887.
[20] H. Jiang, Y. -Z. Cheng, Y. Zhang, S. -Y. Yu, Org. Lett., 2013, 15, 4884-
4887.

Chemistry - A European Journal
10.1002/chem.201602053
COMMUNICATION
Entry for the Table of Contents
COMMUNICATION
Shuang Wang, Wen-Liang Jia, Lin
Wang, Qiang Liu* and Li-Zhu Wu
Page No. – Page No.
Domino Radical Addition/Oxidation
Sequence via Photocatalysis: One-
Pot Synthesis of Polysubstituted
Furans from α-Chloro-Alkyl Ketones
and Styrenes
Text for Table of Contents