Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes

Article abstract of DOI:10.1002/aoc.4159

A ligand free catalytic system consisting of Pd(OAc)₂ (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF₄, exhibit high efficiency in the Mizoroki-Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.

Full text of DOI:10.1002/aoc.4159

Received: 11 July 2017
DOI: 10.1002/aoc.4159
Revised: 30 September 2017
Accepted: 2 October 2017
C O M M U N I C A T I O N
Silver sequestration of halides for the activation of
Pd(OAc)2 catalyzed Mizoroki‐Heck reaction of 1,1 and
1,2 ‐ Disubstituted alkenes
Pronnoy G. Bangar1,2 | Priyanka R. Jawalkar3 | Swapnil R. Dumbre1 | Dharmaraj J. Patil1 |
Suresh Iyer1,2
1 Organic Chemistry Division, National
A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric
quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the
Mizoroki‐Heck arylation, transforming aryl iodides and 1,1 as well as 1,2
disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields
in very short reaction times.
Chemical Laboratory, Dr. Homi Bhabha
Road, Pashan, Pune, Maharashtra 411008,
India
2 Academy of Scientific and Innovative
Research (AcSIR), New Delhi 110025,
India
3 Medicinal Chemistry Department, Sai
Life Sciences Ltd., Chrysalis Enclave,
International Biotech Park, Phase II,
Hinjewadi, Pune 411057, India
KEYWORDS
1,1‐disubstituted alkenes, 1,2‐disubstituted alkenes, AgBF4, AgOAc, Mizoroki‐Heck reaction
Correspondence
Suresh Iyer, Organic Chemistry Division,
National Chemical Laboratory, Dr. Homi
Bhabha Road, Pashan, Pune Maharashtra,
411008, India.
Email: s.iyer@ncl.res.in
Funding information
Council for Scientific and Industrial
Research, Grant/Award Number: ORIGIN
XII Five year Plan CSC 0108
1 | INTRODUCTION
be preferred for its E‐stereoselectivity. A few known syn-
thesis of 1,1,2‐trisubstituted aryl alkenes from the
The Mizoroki‐Heck arylation of monosubstituted alkenes
is a fast and well studied reaction while that of 1,1 and
1,2‐disubstituted alkenes is relatively less explored.
1,1,2 –Trisubstituted and 1,1,2,2,‐tetrasubstituted aryl
alkenes are an important structural motif in several
bioactive molecules, functional materials, OLED and
various organic electroluminiscent devices.[1–7] Several
methodologies are available for the synthesis of these
1,1,2‐ and 1,1,2,2‐ aryl alkenes but they give mixtures
of E‐Z stereoisomers and isomeric purity is essential for
bioactivity.[8–16] Here, the Mizoroki‐Heck reaction could
Mizoroki‐Heck reaction of 1,1 and 1,2‐disubstituted
alkenes[17–24] are sluggish reactions, and/or require
special reagents, bases, ligands and other reaction condi-
tions.[25–30] The Mizoroki‐Heck reaction of stilbenes has
been applied to the synthesis of Tamoxifen.[31] Other
bioactive molecules have been derived from the similar
reaction of aryl halides with dimethyl itaconate ester
and various disubstituted alkenes.[32–35]
The halide sequestration property of stoichiometric
silver salts has been put to advantage in the asymmetric
Mizoroki‐Heck reaction.[36–47] AgOAc has been used in
Appl Organometal Chem. 2017;e4159.
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https://doi.org/10.1002/aoc.4159

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BANGAR ET AL.
the Mizoroki‐Heck reaction of allyl alcohols and
vinyl iodides.[48] One of the recent reports is the Ag2CO3
mediated arylation of fluoroacrylates.[49] So we
experimented on the use of stoichiometric AgOAc for
the Mizoroki‐Heck reaction.[50]
(ratios ranging from 1:0.43 to 6: 1). Here the E‐ isomer
was the major product, resulting in the desired Z‐ stilbene
structural motif, confirmed by 2D NOESY NMR. No
reaction was observed in the absence of AgOAc. Aryl
bromides were unreactive under these conditions.
The Mizoroki ‐ Heck reaction of itaconate ester with
aryl halides and triflates has been shown to give the
2‐(E)‐benzylidene succinates.[34,35] These are excellent
precursors of chiral benzyl succinates which can be
obtained by asymmetric hydrogenation. The AgOAc
protocol gave very high yields of the E ‐ isomer
(also confirmed by 2D NOESY NMR) in very short
reaction times (Table 1).
The AgOAc sequestration with 1,2 –disubstituted
alkenes and aryl iodides gave high isolated yields of the
desired 1,1,2‐trisubstituted aryl alkenes in 1‐ 6 h
(Scheme 2, Table 2). A cationic mechanism is probably
playing a role in the high yielding reaction, with AgOAc
abstraction of the aryl iodide and also a Pd iodide interme-
diate. Various solvents like ethylene glycol, PEG‐200,
PEG‐400 were also suitable for the reaction. AgBF4, which
is a stronger sequestrating agent, with greater affinity for
halides, was also studied (Scheme 3). Reactions were
2 | RESULTS AND DISCUSSION
The addition of stoichiometric AgOAc to the reaction
mixture of 4‐iodo anisole and diphenyl ethene in refluxing
acetic acid as solvent, to our delight gave very high, 84%
isolated yield of the desired product in short reaction time.
No reaction was observed with the use of K2CO3 or NaOAc
instead of AgOAc. The results of the reaction of several
aryl iodides with 1,1 –disubstituted alkenes to give the
1,1,2‐trisubstituted aryl alkenes is shown in Table 1. The
reaction with diphenyl ethene was normally completed
in 2 ‐ 3 h. The reaction of ethyl atropate took 24 h for
completion, while dimethylitaconate ester took 1.5‐6 h
(Table 1), all giving high isolated yields (Scheme 1).
An inseparable mixture of E‐Z isomers was obtained
1
in the reaction with ethyl atropate, observed by H NMR
TABLE 1 Pd(OAc)2 (cat)/AgOAc mediated Mizoroki‐Heck reaction with 1, 1 –disubstituted alkenesa
S.No
Aryl iodide
Alkene
Time, h
Yield, %
Product
1
C6H5I (1a)
2 (DPE)
2
74
3a
2
4‐CH3OC6H4I (1b)
4‐CH3C6H4I(1c)
4‐ClC6H4I(1d)
2
2.5
3
77
56
60
64
89
76
58
69
61
60
57
74
69
89
87
93
74
63
77
98
3b
3
2
3c
4
2
3
3d
5
4‐OCF3C6H4I (1e)
2,4‐FC6H3I(1f)
2‐CH3C6H4I(1 g)
C6H5I (1a)
2
2.5
3
3e
6
2
3f
7
2
2
3g
8
4 (ethyl atropate)
22
24
24
21
22
5
5a(2.4: 1)
5b (6:1)
5c (1:0.43)
5d (3: 1)
5e (3: 1)
7a(E)
7b(E)
7c(E)
7d(E)
7e(E)
7f(E)
7g(E)
7h(E)
7i(E)
9
4‐CH3C6H4I (1c)
4‐ClC6H4I (1d)
4‐FC6H4I(1 h)
4
10
11
12
13
14
15
16
17
18
19
20
21
4
4
2,4‐FC6H3I(1f)
C6H5I (1a)
4
6 (Itaconate)
4‐CH3OC6H4I (1b)
4‐CH3C6H4I (1c)
4‐ClC6H4I (1d)
4‐FC6H4I (1 h)
4‐NO2C6H4I (1i)
2‐CH3C6H4I (1 g)
4‐OCF3C6H4I (1e)
4‐CF3C6H4I (1j)
6
6
6
6
6
6
6
6
1.5
3.5
3
2.5
6
6
2
2
aReaction conditions: DPE (1 mmol), ArI (1 mmol), AgOAc (1.2 Eq), Pd(OAc)2 (5 mol %), AcOH, Argon, Reflux

BANGAR ET AL.
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R
3 a - g 56 - 89 %
COOC2H5
or
or
2
COOC2H5
PdOAc2 (5mol %)
I
R
+
AgOAc (1.2 Eq)
AcOH
R
1 a - j
Reflux, Argon
5 a - e 57 - 69 %
COOCH3
4
COOCH3
COOCH3
COOCH3
R
SCHEME 1 Pd(OAc)2 (cat)/AgOAc
mediated Mizoroki‐Heck reaction with
1, 1 –disubstituted alkenesa
6 (1 mmol)
R : H, 4-OCH3, 4-CH3, 4-Cl, 4-OCF3, 2,4-F, 2-CH3, 4-F, 4-NO2, 4-CF3
7 a - i 59 - 98 %
Pd(OAc)2 (Cat)
AgOAc (1.2 Eq)
I
W
W
+
AcOH, Reflux
Argon
R
R
SCHEME 2 Pd(OAc)2 (Cat)/AgOAc
mediated Mizoroki‐Heck reaction of
1,2‐disubstituted alkenesa
Yield : 64 - 100 %
8 a-e
1 a - c, e, g, k
9 a - l
R : H, 4-OCH3, 4-CH3, 4-OCF3, 2-CH3, 4-COCH3
W : CHO, COOC2H5, COCH3, COC6H5, C6H5
TABLE 2 Pd(OAc)2 (Cat)/AgOAc mediated Mizoroki‐Heck reaction of 1,2‐disubstituted alkenesa
S. No
Aryl halide
Alkene
Time, h
Yield, %
Product (E: Z)
1
C6H5I (1a)
8a
1
89
(9a) ‐
2
4‐CH3OC6H4I (1b)
4‐CH3C6H4I (1c)
4‐CF3OC6H4I (1e)
4‐CH3COC6H4I (1 k)
4‐CH3OC6H4I (1b)
4‐CH3OC6H4I (1b)
2‐CH3C6H4I (1 g)
4‐CH3OC6H4I (1b)
2‐CH3C6H4I (1 g)
4‐CH3C6H4I (1c)
4‐CH3OC6H4I (1b)
8b
8c
8c
8b
8c
8a
8a
8e
8e
8a
8d
1
74
89
(9b)‐3: 1
(9c)‐3: 1
(9d)‐2: 1
(9e)‐8: 1
(9f)‐1: 1
(9 g)‐2: 1
(9 h)‐3: 1
(9i)‐3: 1
(9j)‐3: 1
(9 k)‐4: 1
(9 l)‐2: 1
3
1
4
1
88
5
2
95
6
5
94
7
6
100
64
8
7
9
40 mins
99
10
11
12
6
100
80
40 mins
1
97
aReaction conditions: ArI (1.2 mmol), 1,2‐Disubstituted alkene (1 mmol), AgOAc (1.2 Eq), Pd(OAc)2 (5 mol %), AcOH, Argon, Reflux
Pd(OAc)2 (Cat)
I
AgBF4 (1.2 Eq)
W
W
+
DMF, 100 oC
Argon
R
R
Yield : 51 - 97 %
10 a - j
8 e, b, c, a, d
1 b, c, e, k
SCHEME 3 AgBF4 mediated Pd(OAc)2
catalyzed Mizoroki‐Heck reactiona
R : 4-OCH3, 4-CH3, 4-OCF3, 4-COCH3
W : C6H5, COOC2H5, COCH3, CHO, COC6H5

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BANGAR ET AL.
complete in 2 – 7 h, in DMF as solvent, at 100 °C giving
51–97% yield (Table 3). The use of aryl bromides or even
aryl chlorides is desirable in these reactions but were
unreactive even with Pd[(PPh)3]4 as catalyst.
3,3‐Diphenylacrylaldehyde (9a) (1 h, 0.185 g, 0.89
mmol, 89 %), CAS Registry Number 1210‐39‐5 H NMR
1
(200 MHz, CDCl3, δ) – 9.56‐9.54 (d, 1H), 7.52‐7.28 (m,
10H), 6.64‐6.62 (d, 1H), 13C NMR (200 MHz, CDCl3,
δ)‐ 193.18, 161.92, 139.34, 136.31, 133.37, 128.35,
128.26, 127.98, 126.91 (IR (cm‐1) – 3305, 3019, 2852,
2400, 1660, 1593, 1572, 1492, 1445, 1422, 1389, 1343,
1215, 1156, 1127, 1075, 1046, 768, 701, 668 HRMS‐ESI:
[M++H]+ calculated for C15H13O [M++H]+, found:
209.096
3 | EXPERIMENTAL SECTION
3.1 | General Procedure for AgOAc
mediated monoarylation of 1,1‐
disubstituted or 1,2‐disubstituted alkenes
To a solution of silver acetate (0.2 g, 1.2 mmol) and pal-
ladium acetate (0.011 g, 5 mol %) in acetic acid was
added aryl iodide (1 mmol) and 1,1‐diphenyl ethene
(1 mmol) or cinnamaldehyde (1 mmol). The resulting
mixture was heated to 110 °C for 3 h under argon. After
completion of reaction (monitored by TLC), a saturated
solution of NaHCO3 was added to the reaction mixture
to neutralize the acetic acid. The aqueous solution was
extracted with ethyl acetate (3 x 20 ml) and the combined
extract was washed with brine and dried over Na2SO4.
The organic layer was concentrated under vacuum and
the crude product purified by column chromatography
on silica gel (100–200 mesh, Petroleum ether or
Petroleum ether: 2 – 5 % Ethyl acetate) to give the pure
product.
Ethene‐1,1,2‐triyltribenzene (3a) (2 h, 0.190 g, 0.74
mmol, 74 %) CAS Registry Number 58‐72‐0 1H NMR
(200 MHz, CDCl3, δ)‐ 7.39‐7.23 (m, 10H), 7.19‐7.05
(m, 5H), 7.02 (s, 1H), 13C NMR (200 MHz, CDCl3, δ)‐
143.4, 142.6, 140.3, 137.4, 130.4, 129.5, 128.6, 128.2,
127.9, 127.6, 127.5, 127.4, 126.7, 116.5, 87.5, 83.1, 68.8,
65.1, 64.6 IR (cm‐1) – 3023, 2402, 1597, 1522, 1428, 1216,
1028, 928, 768, 671 HRMS‐ESI: [M++H]+ calculated for
C20H17 [M++H]+ 257.1325 Found: 257.1326
3.2 | General Procedure for AgBF4
mediated monoarylation of
1,2‐disubstituted alkenes
To a solution of AgBF4 (0.234 g, 1.2 mmol) and palladium
acetate (0.011 g, 5 mol %) in DMF under argon, was added
aryl iodide (1.5 mmol) and 1,2‐disubstituted alkene
(1 mmol). The resulting mixture was heated to 100 °C
under argon. After completion of reaction (monitored by
TLC), water was added to quench the reaction. The aque-
ous solution was extracted with ethyl acetate (3 x 20 ml)
and the combined extract was washed with brine and
dried over Na2SO4. The organic layer was concentrated
under vacuum and the crude product purified by column
chromatography on silica gel (100–200 mesh, Petroleum
ether or Petroleum ether: 2 – 5 % Ethyl acetate) to give
the pure product.
4‐Phenyl‐4‐(p‐tolyl)but‐3‐en‐2‐one (10a) (2 h, 0.200 g,
0.85 mmol, 85 %) CAS Registry Number 39092‐21‐2 H
NMR (200 MHz, CDCl3, δ)‐ 7.44‐7.13 (m, 9H),
6.61(s, 1H, E isomer), 6.57 (s, 1H, Z isomer), 2.44 (s, 3H,
Z isomer), 2.39 (s, 3H, E isomer), 1.92 (s, 3H, Z isomer),
1.89 (s, 3H, E isomer) 13C NMR (200 MHz, CDCl3, δ)‐
200.45, 200.18, 154.19, 154.07, 141.04, 139.76, 139.12,
1
TABLE 3 AgBF4 mediated Pd(OAc)2 catalyzed Mizoroki‐Heck reactiona
S. No
Aryl halide
Alkene
Time, h
Yield %
Product (E: Z ratio)
1
4‐CH3OC6H4I (1b)
8e
2
76
(10 a)‐ 2: 1
2
4‐CH3C6H5I (1c)
8c
8b
8b
8b
8d
8d
8e
8a
8a
2
2
5
7
3
3
4
3
3
85
83
91
91
67
83
51
84
97
(10 b)‐ 1: 1
(10 c)‐ 2: 1
(10 d)‐ 14: 1
(10 e)‐ 3: 1
(10 f)‐ 2: 1
(10 g)‐ 2: 1
(10 h)‐ 1: 0.07
(10 i)‐ 2: 1
(10 j)‐ 1: 1
3
4‐CH3COC6H4I (1 k)
4‐CF3OC6H4I (1e)
4‐CH3OC6H4I (1b)
4‐CH3OC6H4I (1b)
4‐CH3COC6H4I (1 k)
4‐CH3COC6H4I (1 k)
4‐CH3OC6H4I (1b)
4‐CH3COC6H4I (1 k)
4
5
6
7
8
9
10
aReaction conditions: ArI (1.5 mmol), 1,2‐Disubstituted alkene (1 mmol), AgBF4 (1.2 Eq), Pd(OAc)2 (5 mol %), DMF, Argon, 100 °C.

BANGAR ET AL.
5 of 6
[14] R. C. Jones, M. Galezowski, D. F. O’Shea, J. Org. Chem. 2013,
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138.84, 137.88, 135.95, 129.57, 129.14, 128.33, 127.55,
126.88, 30.27, 21.21 IR (cm‐1) ‐ 3681, 3374, 3019, 2400,
1644, 1590, 1513, 1422, 1357, 1216, 1117, 1043, 928,
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In summary, the Mizoroki‐Heck arylation of various 1,1‐
and 1,2‐disubstituted alkenes to give 1,1,2‐trisubstituted
aryl alkenes with the bioactive Z‐stilbene and benzylidene
succinate motif has been described using AgOAc and
AgBF4 as sequestrating agents, in very high yields and
short reaction times. The non Ag mediated reactions are
also being investigated.
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Organomettalics 2003, 22, 4193.
Financial support from the CSIR Network Project,
ORIGIN – under XII Five year plan CSC 0108 is gratefully
acknowledged and PGB thanks the UGC for a SRF.
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How to cite this article: Bangar PG, Jawalkar
PR, Dumbre SR, Patil DJ, Iyer S. Silver
sequestration of halides for the activation of
Pd(OAc)2 catalyzed Mizoroki‐Heck reaction of 1,1
and 1,2 ‐ Disubstituted alkenes. Appl Organometal
Chem. 2017;e4159. https://doi.org/10.1002/aoc.4159
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