Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated ketones

Article abstract of DOI:10.1016/j.cclet.2019.09.017

An efficient method was developed for the conjugate addition of water to various α,β-unsaturated ketones by using bismuth(III) chloride as a catalyst. The reactions proceeded smoothly in the presence of a catalytic amount of BiCl₃ (20 mol%) in aqueous media to furnish a variety of synthetically useful β-hydroxyl ketones in moderate to good yields. Apart from water molecule, various alcohols could also be employed as nucleophiles to react with α,β-unsaturated ketones, leading to β-alkoxyl ketones in modest to high yields. In addition, the mild reaction conditions also entailed the conjugate addition reactions to proceed with the tolerance to a range of functional groups.

Full text of DOI:10.1016/j.cclet.2019.09.017

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Contents lists available at ScienceDirect
Chinese Chemical Letters
journal homepage: www.elsevier.com/locate/cclet
Communication
Bismuth trichloride-catalyzed oxy-Michael addition of water and
alcohol to α,β-unsaturated ketones
Zhen Wua,b, Xue-Xin Fenga,b, Qing-Dong Wangb, Jin-Jin Yuna, Weidong Raoc,
a,
Jin-Ming Yanga,b, , Zhi-Liang Shen
*
*
a
School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
School of Pharmacy, Yancheng Teachers University, Yancheng 224007, China
Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
b
c
A R T I C L E I N F O
A B S T R A C T
Article history:
Received 22 June 2019
Received in revised form 27 August 2019
Accepted 9 September 2019
Available online xxx
An efficient method was developed for the conjugate addition of water to various α,β-unsaturated
ketones by using bismuth(III) chloride as a catalyst. The reactions proceeded smoothly in the presence of
a catalytic amount of BiCl3 (20 mol%) in aqueous media to furnish a variety of synthetically useful
β-hydroxyl ketones in moderate to good yields. Apart from water molecule, various alcohols could also be
employed as nucleophiles to react with α,β-unsaturated ketones, leading to β-alkoxyl ketones in modest
to high yields. In addition, the mild reaction conditions also entailed the conjugate addition reactions to
proceed with the tolerance to a range of functional groups.
Keywords:
Bismuth trichloride
Water
β-Hydroxyl carbonyl compound
Michael addition
Functional group tolerance
© 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Published by Elsevier B.V. All rights reserved.
β-Hydroxyl carbonyl compounds, which are structural motif
widely found in numerous natural products, play an important role
in organic chemistry as versatile synthetic intermediates [1,2].
Besides the well-known Aldol reaction between aldehyde and
ketone which serves as a practical method for the synthesis of
β-hydroxyl carbonyl compounds [2], β-hydroxyl carbonyl
compounds could also be constructed by a two-step reaction
sequence [3]. However, these methods suffered either from the
production of undesired products due to the relatively strong basic
reaction conditions or from the comparatively low efficiency of
multi-step synthesis. In this context, the direct addition of water to
α,β-unsaturated carbonyl compound [4]. It was not until 2003 that
Bergman and Toste had reported an efficient phosphine-catalyzed
reaction of alcohol/water with α,β-unsaturated carbonyl com-
pound by means of in situ forming a strong base as reaction catalyst
[5]. However, only one case using water as a reaction nucleophile
was reported in their protocol. Thereafter, Feringa and Roelfes
reported an enantioselective Michael-type reaction of water with
specific α,β-unsaturated 2-acyl imidazole/pyridine by employing
DNA-supported copper catalyst or artificial metalloenzymes as
reaction promoter [6]. More recent studies from the Hanefeld
group have revealed that amino acid or enzyme is also able to
catalyze the oxy-Michael reaction of water with cyclic enones or
lactones with moderate success (mostly in low to modest yields),
further implying the difficulty of realizing the transformation [7,8].
Very recently, our group described that a catalytic amount of In
(OTf)3 or CrCl3 are capable of catalyzing the reaction between
water and α,β-unsaturated ketones in aqueous media, providing an
effective method for the synthesis of β-hydroxyl ketones [9].
In recent decades, bismuth(III) salts have been demonstrated to
be efficient catalysts for effecting various organic transformations
due to their powerful Lewis acidity [10]. As a continued task of our
group to develop organic reactions in aqueous media [11–13],
herein we report an efficient method for the synthesis of
β-hydroxyl carbonyl compounds via a bismuth(III)-catalyzed direct
addition of water to α,β-unsaturated carbonyl compound. The
reactions proceeded smoothly in aqueous media to furnish a
α,β-unsaturated carbonyl compounds,
a commonly occurred
reaction which widely exists in living organism, provides an easy
and direct entry to β-hydroxyl carbonyl compounds via a Michael-
type reaction pathway, along with the inhibition of undesired side
reactions. However, the reaction of water with α,β-unsaturated
carbonyl compounds constitutes a big challenge because the
reaction is an equilibrium and the formed β-hydroxyl carbonyl
compound has
a strong tendency to undergo β-hydroxyl
elimination to regenerate the original substrate of more stable
* Corresponding authors at: School of Chemistry and Molecular Engineering,
Nanjing Tech University, Nanjing 211816, China.
E-mail addresses: yangjm@yctu.edu.cn (J.-M. Yang), ias_zlshen@njtech.edu.cn
(Z.-L. Shen).
https://doi.org/10.1016/j.cclet.2019.09.017
1001-8417/© 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
Please cite this article in press as: Z. Wu, et al., Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated
ketones, Chin. Chem. Lett. (2019), https://doi.org/10.1016/j.cclet.2019.09.017

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Table 2
variety of synthetically useful β-hydroxyl ketones in moderate to
good yields, along with the tolerance to a range of functional
groups. Aside from water, alcohols could also be employed as
nucleophiles to react with a wide range of α,β-unsaturated ketones,
leading to β-alkoxyl ketones in modest to high yields.
Substrate scope study by using various enones.a
In the beginning, an array of bismuth(III) salts were employed
to investigate their catalytic activity in the Michael-type reaction
of 1-phenylprop-2-en-1-one (1a) with water. The reactions were
carried out at 80 ꢀC for 24 h in aqueous acetonitrile in the presence
of 20 mol% bismuth(III) salts. As shown in Table 1, among the
various bismuth(III) salts surveyed (entries 1–9), BiCl3 exhibited
the best catalytic performance to afford the corresponding product
2a in 72% yield (entry 1). In contrast, the use of bismuth(III) salts
containing other anions led to decreased product yields (entries
2–9). Further studies of other reaction parameters, including
reaction temperature and reaction time (entries 10–14), showed
that the reaction worked with best performance when it was
performed at 80 ꢀC for 24 h by employing BiCl3 as reaction catalyst.
Subsequently, the substrate scope of the reaction was surveyed
by using a variety of structurally diverse α,β-unsaturated ketones
as starting materials. As summarized in Table 2, different types of
electron-deficient alkenes were applicable to the present conju-
gate addition, affording the corresponding products in modest to
good yields. Not only aryl enones containing electron-withdrawing
groups (including CN, COOMe, F, Cl, and Br) in the benzene ring, but
also aryl enones containing electron-donating substituents (in-
cluding Me, OMe, and OCH2O) in the benzene ring were capable of
efficiently participating in the 1,4-addition reaction to furnish the
expected product 2b-k in 34%-84% yields (entries 1-10). In addition
to aryl substituted enones, enones 1l-n possessing heteroaryl
substituents were amenable to the mild reaction conditions, giving
rise to the anticipated products 2l-n in moderate to good yields
(46%-89% yields, entries 11-13). Moreover, alkyl substituted enones
1o-p reacted in the same manner to afford the desired β-hydroxyl
carbonyl compounds 2o-p in acceptable yields (42%-54% yields,
entries 14 and 15). When (E)-1-phenylbut-2-en-1-one (1q)
Entry
1
Substrate
Product
Yield (%)b
59
2b
2
3
2c
34
83
2d
4
5
6
7
2e
2f
53
64
66
84
2g
2h
8
2i
75
Table 1
Optimization of reaction conditions.a
9
2j
58
71
10
2k
Entry
Catalyst
Temp (oC)
Time (h)
Yield (%)b
1
2
3
4
5
6
7
8
BiCl3
BiBr3
BiI3
BiF3
BiONO3
Bi(OTf)3
Bi(NO3)3
Bi(OAc)3
Bi2(SO4)3
BiCl3
80
80
80
80
80
80
80
80
80
r.t.
50
100
80
80
24
24
24
24
24
24
24
24
24
24
24
24
12
36
72 (70)c
2
58
17
41
66
54
22
57
14
11
12
13
2l
89
82
46
2m
2n
9
10
11
12
13
14
BiCl3
BiCl3
BiCl3
BiCl3
47
10
59
64
14
2o
54
a
Unless otherwise noted, the reactions were performed at 80 ꢀC for 24 h by using
1-phenyl-prop-2-en-1-one (1a, 1 mmol) and bismuth(III) salt (0.20 mmol) in
CH3CN/H2O (1 mL/2 mL).
15
16
2p
2q
42
40
b
Yield was determined by NMR analysis of the crude reaction mixture by using
1,4-dimethoxy-benzene as an internal standard.
c
Isolated yield.
Please cite this article in press as: Z. Wu, et al., Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated
ketones, Chin. Chem. Lett. (2019), https://doi.org/10.1016/j.cclet.2019.09.017

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3
Table 4
Table 2 (Continued)
Substrate scope study by using cyclic enones and various alcohols.a
Entry
17
Substrate
Product
Yield (%)b
0
2r
Entry
Substrate
ROH
Product
Yield (%)b
1
2
1s
1t
EtOHc
4 m
4n
15
91
EtOHc
a
i-PrOHc
4o
4p
43
85
The reactions were performed at 80 ꢀC for 24 h by using enone 1 (1 mmol) and
3
4
1t
1t
BiCl3 (0.20 mmol) in CH3CN/H2O (1 mL/2 mL).
b
Isolated yield.
5
1t
4q
50
a
Unless otherwise noted, the reactions were performed at room temperature for
containing a methyl group at its β position was used as substrate,
the addition reaction proceeded with reduced efficiency to give the
product 2q in 40% yield (entry 16), presumably due to steric
hindrance. In sharp contrast, no reaction occurred when enone 1r
bearing a methyl group at its α position was utilized as reactant
(entry 17).
Next, the substrate scope of the reaction was further surveyed
by using various alcohols as nucleophiles [14]. As shown in Table 3,
the conjugate addition involving enone 1 h and various alcohols 3
proceeded smoothly to give the corresponding products 4a-l in
moderate to good yields. Besides alkyl alcohols (entries 1-6), allylic
alcohol (entry 7), propargylic alcohol (entry 8), and benzyl alcohols
(entries 9 and 10) were also demonstrated to be efficient substrates
for the transformation, leading to the anticipated products 4g-j in
moderate to good yields. In addition to primary alcohols,
secondary alcohols (entries 2 and 11) also efficiently participated
24 h by using cyclic enones 1 s-t (1 mmol), alcohol
3 (6 mmol), and BiCl3
(0.20 mmol) in CH3CN (1 mL).
b
Isolated yield.
c
The reaction was directly performed in alcohol (ROH, 3 mL) instead of in CH3CN.
in the addition reactions to produce the products 4b and 4k in
moderate yields. In the same fashion, chiral alcohol of menthol
could also be smoothly converted into the corresponding β-alkoxyl
ketone 4l in an acceptable yield (entry 12). However, when
relatively acidic phenol was employed as a nucleophile to react
with enone 1 h under the optimized reaction conditions, only a
trace amount of the desired product could be detected, probably
owing to the poorer nucleophilicity of phenol when compared to
aliphatic alcohols. It is worth mentioning that the mild reaction
conditions entailed the presence of various important functional
groups or substituents embedded in the starting materials,
including chloro, cyano, ethoxycarbonyl, C = C, and CꢁC.
Besides linear enones, cyclic enones could also be employed as
substrates. As listed in Table 4, six-membered enone 1s reacted
with ethanol with usual poor performance, leading to the desired
product 4 m only in 15% yield (entry 1). In sharp contrast, the
reactions involving seven-membered enone 1t and some typical
alcohols 3 proceeded with enhanced efficiency to give the target
products 4n-q in moderate to high yields (entries 2-5). However,
the reaction of cyclopentenone with ethanol could not afford the
desired product, presumably because of the instability of the in situ
formed β-hydroxyl ketone which has the strong tendency to
undergo β-elimination.
In a nutshell, an efficient method for achieving the conjugate
addition of water with various α,β-unsaturated ketones was
developed. The reactions proceeded smoothly in the presence of
a catalytic amount of BiCl3 (20 mol%) in aqueous media to furnish a
variety of synthetically useful β-hydroxyl ketones in moderate to
good yields. Apart from water, various alcohols could also be
Table 3
Substrate scope study by using various alcohols.a
Entry
ROH
Product
Yield (%)b
1
2
3
4
EtOHc
4a
4b
4c
4d
96
91
91
93
i-PrOHc
n-BuOHc
5
6
7
8
4e
4f
90
96
72
81
employed as nucleophiles to react with
a wide range of
4g
4h
α,β-unsaturated ketones, leading to β-alkoxyl ketones in modest
to high yields. In addition, the mild reaction conditions also
allowed the conjugate addition reactions to proceed with the
tolerance to a range of functional groups.
9
PhCH2OH
4i
4j
93
81
10
Acknowledgments
11
12
PhCH(CH3)OH
4k
4 l
42
46
We gratefully acknowledge the financial support from Nanjing
Tech University (Start-up Grant No. 39837118), Yancheng Teachers
University, and Nanjing Forestry University.
a
Unless otherwise noted, the reactions were performed at 80 ꢀC for 24 h by using
1-(4-methoxyphenyl)prop-2-en-1-one (1 h, 1 mmol), alcohol 3 (6 mmol) and BiCl3
(0.20 mmol) in CH3CN (1 mL).
Appendix A. Supplementary data
b
Supplementarymaterialrelatedtothisarticlecanbefound, inthe
online version, at doi:https://doi.org/10.1016/j.cclet.2019.09.017.
Isolated yield.
c
The reaction was directly performed in alcohol (ROH, 3 mL) instead of in CH3CN.
Please cite this article in press as: Z. Wu, et al., Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated
ketones, Chin. Chem. Lett. (2019), https://doi.org/10.1016/j.cclet.2019.09.017

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Please cite this article in press as: Z. Wu, et al., Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated
ketones, Chin. Chem. Lett. (2019), https://doi.org/10.1016/j.cclet.2019.09.017