Direct synthesis of alkenyl iodides: Via indium-catalyzed iodoalkylation of alkynes with alcohols and aqueous HI

Article abstract of DOI:10.1039/c8ob00183a

A convenient and efficient indium-catalyzed approach to synthesize alkenyl iodides has been developed through direct iodoalkylation of alkynes with alcohols and aqueous HI under mild conditions. This catalytic protocol offers an attractive approach for th

Full text of DOI:10.1039/c8ob00183a

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DOI: 10.1039/C8OB00183A
Journal Name
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PAPER
Direct construction of alkenyl iodides via indium-
catalyzed iodoalkylation of alkynes with alcohols and
aqueous HI
Cite this: DOI: 10.1039/x0xx00000x
Chao Wua,c, Zheng Wanga, Zhan Hua, Fei Zenga, Xing-Yu Zhanga, Zhong Caoc, Zilong Tangd,
Wei-Min He*a,b and Xin-Hua Xub
Received 00th January 2012,
Accepted 00th January 2012
A convenient and efficient indium-catalyzed approach to alkenyl iodides has been developed through
direct iodoalkylation of alkynes with alcohols and aqueous HI under mild conditions. This catalytic
protocol offers an attractive approach to a diverse range of alkenyl iodides in good to excellent yields.
DOI: 10.1039/x0xx00000x
www.rsc.org/
In 2012, Ji group disclosed an iron mediated method for the
Introduction
construction of alkenyl iodides via coupling reaction of
Alkenyl iodides are very important compounds in organic
synthesis,1 and they have attracted increasingly synthetic
pursuit of chemists due to their wide application as building
blocks in transition-metal-catalyzed cross-coupling reactions
such as Heck, Suzuki, Stille, Sonogashira, and Negishi
reactions.2 In general, classical preparation of alkenyl iodides
relies heavily on the hydroiodination of alkynes with iodinating
reagents such as PI3, HI or AcI.3,4 For access to the versatile
functionalized alkenyl iodides, various synthetic methods on
alkynic iodoalkylation have been developed over the past
decades, such as Ti, Zr, or Ni salts mediated the coupling of
organometallic reagents or unsaturated compounds with
alkynes followed by iodination of the resulting alkenyl
organometallics,5-10 the intramolecular reaction of complicated
alkynes such as substituted propargylic aryl ethers or 1, 5-
enynes11 radical addition of perfluoroalkyl iodides to alkynes
induced by radical initiators,12 and the use of activated alkynes
such as ethyl propiolate or α, β-acetylenic ketones reacted
with iodide salts and ketones or aldehydes to access alkenyl
iodides.13 Nevertheless, most of these methods are
accompanied with limitations such as need stoichiometric
organometallic reagents, extra steps to prepare the starting
materials, multistep reactions, poor substrate scope, and harsh
reaction conditions. Therefore, the development of simple,
mild, convenient, and efficient method to access alkenyl
iodides from simple and readily available starting materials is
still highly desirable.
alcohols and alkynes in the presence of I2 (1 equiv) and NaI (2
equiv) (Scheme 1b).16 Nevertheless, the use of a stoichiometric
amount of iron powder may limit their wide applications on a
large scale in the synthetic and pharmaceutical chemistry.
With our continuing interest in alkyne chemistry17 and green
organic synthesis18, herein, we wish to report a new and
efficient InI3 (2.5 mol%) catalyzed approach for the synthesis of
alkenyl iodides through direct iodoalkylation of alkynes with
alcohols and aqueous HI (Scheme 1c). This methodology
provides a practical and highly attractive approach to a diverse
range of alkenyl iodides in good to excellent yields.
Scheme 1 Construction of alkenyl halides.
Results and discussion
Recently, some elegant methods have been developed for
the synthesis of alkenyl halides through the direct coupling
reaction of benzyl alcohols and alkynes by using of FeX3 (> 33.3
equiv, X = Cl, Br) as promoters and halide sources (Scheme
1a).14 However, the synthesis of alkenyl iodides could not be
achieved by this procedure due to the unavailability of FeI3.15
Initially, FeI2 (10 mol%) was added to a mixture of
benzhydrol 1a and phenylacetylene 2a in the presence of
aqueous HI at 60oC (Table 1, entry 1) in 1, 2-dibromoethane
(DBE), the desired product 4a was obtained in only 10% yield.
Subsequently, the catalytic activity of other metal catalysts
This journal is © The Royal Society of Chemistry 2013
J. Name., 2013, 00, 1-3 | 1

Organic & Biomolecular Chemistry
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VJieowuArrtnicalelONnlainme e
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DOI: 10.1039/C8OB00183A
including Au, Ag, Al, Zn, Bi, Cu, and In salts (10 mol %) was were obtained in good to excellent yields
investigated in this reaction system (Table 1, entries 2-9). Phenylethanol derivatives could also be used in the reaction to
Among above metal salts examined, InI3 was found to be the give the expected products in good yields (4e 4h). Notably,
(4a-4d). 1-
-
most effective catalyst for this coupling reaction (89% yield) allylic alcohols such as cyclohex-2-enol and (E)-1, 3-
(Table 1, entry 8). The investigation of solvent effect showed diphenylprop-2-en-1-ol reacted well with phenylacetylene,
that halogenated solvents such as DBE, 1, 2-dichloroethane leading to 1-iodo-1, 4-diene derivatives in 88% and 67% yields,
(DCE), and dichloromethane (DCM) were better than non- respectively (4i and 4j). In addition, tertiary alcohols were
halogenated solvents (Table 1, entries 8, 11-15). Interestingly, usually employed for construction of fully substituted carbon
further optimization suggested that excellent yield (92%) was centres in synthetic chemistry.19 Nevertheless, when tertiary
obtained even when the catalyst loading was reduced to 2.5 alcohol such as 2-phenylpropan-2-ol was used in the present
mol % (Table 1, entry 16). The optimized reaction temperature reaction system, only a trace amount of the desired product 4k
is 60oC. The low yield was observed when the reaction was was obtained. With respect to alkynes, substituted
performed at room temperature (Table 1, entry 18). In phenylacetylenes with either electron-rich or electron-
addition, the direct use of InI3 (33.3 mol %) as catalyst and deficient groups were also compatible with this reaction and
halide source could also promote this reaction but the desired generated the corresponding products in moderate to
product 4a was obtained in relatively lower yield (70%) (Table
Table 2. Reaction Scopea
1, entry 20).
R1
Ar
OH
R2
Ar
Table 1. Optimization of reaction conditionsa
InI3 (2.5 mol%)
+
I
H
+
R2
I
R1
R3
R3
1
2
4
Ph Ph
Ph Ph
Ph Ph
I
I
I
Ph
Yieldb (%)
10
H
H
Entry
1
Cat. (mol %)
FeI2 (10)
Solvent
T(℃)
H
Me
Cl
BrCH2CH2Br
60
4a
E:Z
4b
E:Z
4c
(92 %),
(90:10)
(86 %),
(91:9)
(77 %), (85:15)
E:Z
2
3
4
AuI (10)
AgI (10)
AlI3 (10)
ZnI2(10)
BrCH2CH2Br
BrCH2CH2Br
BrCH2CH2Br
60
60
60
4
Me Ph
Me Ph
N.R.
32
Ph
I
I
Ph
I
H
5
6
7
8
BrCH2CH2Br
BrCH2CH2Br
BrCH2CH2Br
BrCH2CH2Br
60
60
60
60
trace
N.R.
21
H
E:Z
Me
H
BiI3 (10)
CuI (10)
4d
E:Z
4e
4h
4f
E:Z
(88:12)
(91 %),
(92:8)
(86 %),
(89:11)
(83 %),
(88 %),
Me Ph
nBu Ph
Ph
InI3 (10)
89
I
I
I
Ph
In(OAc)3 (10)
9
BrCH2CH2Br
BrCH2CH2Br
ClCH2CH2Cl
CH2Cl2
60
60
60
60
60
60
60
60
60
25
80
60
82
80
H
Cl
H
E:Z
H
10
11
12
13
14
15
16
17
18
19
20
In(OTf)3 (10)
InI3 (10)
InI3 (10)
InI3 (10)
InI3 (10)
InI3 (10)
InI3 (2.5)
InI3 (1)
4g
E:Z
4i
E:Z
(84 %),
(88:12)
(80 %),
(87:13)
(82:18)
71
Ph
82
Ph Ph
Ph Ph
Ph
CH3CN
N.R.
32
I
Me
I
Ph
Toluene
I
H
H
H
DMF
N.R.
92
4l
E:Z
(90:10)
(84 %),
4k
(trace)
4j
E:Z
(67 %),
(84:16)
BrCH2CH2Br
BrCH2CH2Br
BrCH2CH2Br
BrCH2CH2Br
BrCH2CH2Br
F
74
Ph
InI3 (10)
InI3 (10)
InI3 (33.3%)
36
Ph
Me
Ph
Cl
Ph
Ph
Ph
92
70c
I
H
I
H
I
H
a Reaction conditions: benzhydrol 1a (0.5 mmol), phenylacetylene 2a (0.75
mmol), 47 % aqueous HI (1.5 equiv.), catalyst (1-10 mol%), solvent (1 mL),
25-80oC, 6 h. b Isolated yields of the E:Z mixtures. c Without of 47% aqueous
HI.
4n
E:Z
(76 %),
(90:10)
4o
E:Z
(87:13)
(60 %),
4m
E:Z
(90 %),
(87:13)
S
Ph Ph
Ph
Ph
Ph
Ph
I
Ph
Me
I
I
H
H
With the standard reaction conditions in hand, the
generality of this reaction was tested and the results are
summarized in Table 2. Generally, the desired products were
obtained in good yields and with E isomers as the main
products. Diphenylmethanol and its derivatives were suitable
for this protocol, and the corresponding coupling products
4q (62 %), E:Z (85:15)
4p (90 %), E:Z (76:24)
4r
E:Z
(78:22)
(89 %),
Ph Ph
I
Ph
Et
4s
E:Z
(93 %),
(90:10)
a Reaction conditions: alcohols 1 (0.5 mmol), alkynes 2 (0.75 mmol), InI3 (2.5
2 | J. Name., 2012, 00, 1-3
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View Article OPnAliPneER
DOI: 10.1039/C8OB00183A
mol %), 47 % aqueous HI (1.5 equiv.), DBE (1 mL), 60oC, 6 h. b Isolated yields
Scheme 3. Proposed mechanism
. Finally, the alkenyl cation
was attacked by I– to give
an E/Z mixture of the alkenyl iodides (E isomer as the major
product). In Path B, alcohol was converted to the
corresponding dimeric ether . Then, alkyne was alkylated by
producing the alkenyl cation and alcohol in the presence
of InI3/HI. Finally, the iodide ion reacted with alkenyl cation
of the E:Z mixtures; the E:Z ratio was determined by 1H NMR).
cation
8
8
excellent yields
(4l-4o). Heteroaryl alkyne such as 3-
4
ethynylthiophene was also tolerated in this reaction, giving the
desired product 4p in 90% yield. When 1-ethynylcyclohexene
was used as the substrate, the expected product 4q was
obtained in moderate yield. As expected, internal aromatic
alkynes such as 1-phenyl-1-propyneand 1-phenyl-1-butyne
could also be transformed to the corresponding alkenyl iodides
1
5
2
5
8
1
8
gave the desired product 4.
Conclusions
(4r and 4s) in high yields.
In our research on the possible mechanism of this reaction,
In conclusion, a simple and practical catalytic method has
been successfully developed for the construction of alkenyl
iodides from alcohols and alkynes by using of cheap and easily
available aqueous HI as iodide source. Through this
methodology, various alkenyl iodides could be conveniently
and efficiently obtained in good to excellent yields from readily
available starting materials. The present protocol avoids the
direct usage of a stoichiometric amount of metal reagents,
which is expected to expand the potential applications of
alkenyl iodides in pharmaceutical and synthetic chemistry.
Studies on the detailed mechanism and further applications of
this method are under investigation in our laboratory.
dimeric ether 5a was isolated together with the product 4a
when the reaction was carried out for 0.5h (Scheme 2a).
Furthermore, when the reaction of dimeric ether 5a with
phenylacetylene 2a and HI was conducted under the standard
conditions, the desired target 4a was obtained in 85% yield
(Scheme 2b). The above results suggested that dimeric ether
might be the key intermediate in the present reaction system.
Acknowledgements
Scheme 2. Control Experiments
We are grateful for financial support from the National
Natural Science Foundation of China (Nos 21372070,
21273068, 21545010 and 21302048), Scientific Research
Hunan Provincial Education Department (No. 15C0464),
Science and Technology Innovative Research Team in Higher
Educational Institutions of Hunan Province (2012-318) and the
Construct Program of the Key Discipline in Hunan Province.
Based on the experimental results and previous studies,15-
16,20 two postulated pathways of this reaction are proposed as
shown in Scheme 3. In path A, alcohol
to form complex , which would lead to the formation of a
carbocation intermediate in the presence of HI. Then, the
1 was activated by InI3
6
7
addition of carbocation intermediate 7 to alkyne 2 gave alkenyl
Ar
H2O
InI4
Notes and references
2
R3
aHunan Provincial Engineering Research Center for Ginkgo biloba
，
R1
R2
Hunan University of Science and Engineering, Yongzhou 425100, China
bState Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan
University, Changsha, 410082, China
HI
InI3
7
R2
cHunan Provincial Key Laboratory of Materials Protection for Electric
O
H
Ar
Path A
InI4
R1
R1
R2
Power and Transportation, Changsha University of Science and
6
R3
8
Technology, Changsha, 410114, China
dKey Laboratory of Theoretical Organic Chemistry and Functional
Molecule of Ministry of Education, Hunan University of Science and
Technology, Xiangtan 411201, China
OH
R2
Product 4
R1
InI3
1
1
Product 4
E-mail: weiminhe2016@yeah.net
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/b000000x/
H2O
R2
R2
R2
Path B
Ar
InI4
1
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