Carbon Tetrabromide/Triphenylphosphine-Activated Beckmann Rearrangement of Ketoximes for Synthesis of Amides

Article abstract of DOI:10.1002/cjoc.201700191

An efficient Beckmann rearrangement of ketoximes was developed using carbon tetrabromide/triphenylphosphine as an organocatalyst without addition of any acids or metals. The reaction showed good functional group tolerance and gave various amides in moderate to good yields.

Full text of DOI:10.1002/cjoc.201700191

COMMUNICATION
DOI: 10.1002/cjoc.201700191
Carbon Tetrabromide/Triphenylphosphine-Activated Beck-
mann Rearrangement of Ketoximes for Synthesis of Amides
Peng Gao* and Zijing Bai
Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering,
Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, China
An efficient Beckmann rearrangement of ketoximes was developed using carbon tetrabromide/triphenylphos-
phine as an organocatalyst without addition of any acids or metals. The reaction showed good functional group tol-
erance and gave various amides in moderate to good yields.
Keywords Beckmann rearrangement, oganocatalyst, ketoximes, amides
Introduction
Scheme 1 Selected examples of organocatalytic Beckmann
rearrangement of ketoximes
The Beckmann rearrangement is regarded as a versa-
tile method to convert ketoximes into amides due to its
excellent functional group tolerance, chemo-selectivity
and high efficiency.[1] Generally, the reaction proceeds
in the presence of strong Brønsted acids or in dehydrat-
ing medias.[2] However, sensitive substrates cannot be
tolerable and large amount of byproducts may be pro-
duced under the conditions. To circumvent these limita-
tions, a lot of Lewis acids such as AlCl3•6H2O, HgCl2,
InCl3 and BF3•Et2O, have been used as catalysts for the
transformation.[3] In the past decades, in response to the
concern for the development of environmentally benign
chemical processes, organocatalytic methods have be-
come a powerful tool in the Beckmann rearrangement
reactions.[4] Ishihara and co-workers first reported the
reaction could be promoted by catalytic amount of cy-
anuric chloride (TCT) and ZnCl2.[4a] Deng and
co-workers developed a variety of systems to convert
ketoximes to amides and (2-oxo-3-oxazolidinyl) phos-
phinic chloride (BOP-Cl) and TsCl were used as or-
ganocatalysts.[4b,4d] The Ishii group successfully ob-
tained amides from ketoximes in the presence of
1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-chloride
(TAPC).[4c] Lambert presented a 3,3-dichloro-1,2-di-
phenylcyclopropene (CPI-Cl)-activated Beckmann re-
arrangement and a self-propagation mechanism was
proposed.[4e] Despite the great advantages of these
transformations, some problems including the use of
sensitive catalysts or additives, and requirement of
Lewis acid co-catalysis or special solvents, limited their
applications. Thus, further development of organocata-
lytic Beckmann rearrangement is still highly desirable.
As known, carbon tetrabromide and triphenyl-
phosphine was used as a bromination reagent in Corey-
Fuchs[5] and Appel reactions.[6] In recent years, carbon
tetrabromide/triphenylphosphine system was further
developed as an effecient catalyst in the ring-expanding
of cyclopropyl amides,[7] deprotection of O-t-Boc phe-
nols,[8] acetalization of aldehydes,[9] Friedel-Crafts al-
kylation of indoles,[10] and multicomponent reactions.[11]
In consideration of these unique reactivities of carbon
tetrabromide/triphenylphosphine catalytic system and
the special structures of the organocatalysts in the
Beckmann rearrangement reactions, we reasoned that
the versatile carbon tetrabromide/triphenylphosphine
system may be reactive in the Beckmann rearrangement
of ketoximes. Carbon tetrachloride/triphenylphosphine-
mediated Beckmann rearrangements were reported sev-
eral decades ago, but the strategies depended on the uti-
lization of stoichiometric or excess amounts of carbon
tetrachloride and triphenylphosphine as dehydration
reagent.[2j,2k] Moreover, these procedures required extra
*
E-mail: gaopeng_hx@bjwlxy.edu.cn
Received March 17, 2017; accepted May 14, 2017; published online XXXX, 2017.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc. 201700191 or from the author.
Chin. J. Chem. 2017, XX, 1—5
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1

Gao & Bai
COMMUNICATION
water to convert the imidoyl chloride intermediates to
amides. Although triphenylphosphine with other ha-
lo-containing compounds such as iodine[4i] and NBS[4j]
also were used in the Beckmann rearrangements, con-
tinuous efforts are still required in this field. Herein, we
reported an amide synthesis method via Beckmann re-
arrangement of ketoximes using 10% carbon tetrabro-
mide and 10% triphenylphosphine as a catalyst.
7.41－7.44 (m, 2H), 7.24－7.27 (m, 3H), 2.15 (s, 3H);
13C NMR (100 MHz, CDCl3) δ: 168.2, 136.4, 129.0,
121.0, 110.0, 24.5.
N-(4-Bromophenyl)acetamide (2h)[3b]
White
solid (145 mg, 68% yield). 1H NMR (400 MHz, CDCl3)
δ: 7.36－7.42 (m, 4H), 2.15 (s, 3H); 13C NMR (100
MHz, CDCl3) δ: 168.2, 136.9, 131.9, 121.3, 116.8, 24.6.
N-(4-(Trifluoromethyl)phenyl)acetamide
(2i)[2e]
1
White solid (104 mg, 51% yield). H NMR (400 MHz,
CDCl3) δ: 7.53－7.62 (m, 5H), 2.19 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ: 168.6, 140.9, 126.2 (q, J＝3.8 Hz),
125.4, 122.7, 119.3, 24.6.
Experimental
Materials
N-Phenylp ropionamide (2j)[3b]
Light yellow
All solvents and reagents were commercially availa-
ble. Solvent was dried by distillation and stored with 3
Å molecular sieve. 1H NMR spectra were obtained with
tetramethylsilane (TMS, δ＝0) as internal standard in
CDCl3 using an Agilent DD2 400-MR spectrometer
(400 MHz). 13C NMR spectra were recorded on an Ag-
ilent DD2 400-MR spectrometer (100 MHz). The
chemical shifts were determined in the δ-scale relative
to CDCl3 (δ＝77.0). HR-MS was recorded on an AB
SCIEX TOFTM 4600 MS equipped with an electro-
spray ionization (ESI) probe operating in positive ion
mode. PE refers to the fraction boiling at 60－90 ℃.
The amides and lactam products are known compounds
with physical and spectral properties in agreement with
those reported in the literature closely.
solid (124 mg, 83% yield). 1H NMR (400 MHz, CDCl3)
δ: 7.50 (d, J＝8.0 Hz, 2H), 7.42 (br, 1H), 7.28 (t, J＝7.9
Hz, 2H), 7.07 (t, J＝7.4 Hz, 1H), 2.37 (q, J＝7.5 Hz,
2H), 1.22 (t, J＝7.6 Hz, 3H); 13C NMR (100 MHz,
CDCl3) δ: 172.1, 138.0, 128.9, 124.1, 119.8, 30.7, 9.7.
N-(p-Tolyl)propionamide (2k)[12]
White solid
1
(127 mg, 78% yield). H NMR (400 MHz, CDCl3) δ:
7.42 (br, 1H), 7.38 (d, J＝8.2 Hz, 2H), 7.08 (d, J＝8.1
Hz, 2H), 2.34 (q, J＝7.6 Hz, 2H), 2.28 (s, 3H), 1.21 (t,
13
J＝7.6 Hz, 3H); C NMR (100 MHz, CDCl3) δ: 172.0,
135.5, 133.7, 129.4, 119.9, 30.6, 20.8, 9.7.
N-(4-Chlorophenyl)propionamide (2l)[13] Light
1
yellow solid (130 mg, 71% yiled). H NMR (400 MHz,
CDCl3) δ: 7.45 (d, J＝8.8 Hz, 2H), 7.23－7.27 (m, 2H),
7.19 (br, 1H), 2.37 (q, J＝7.5 Hz, 2H) 1.22 (t, J＝7.5 Hz,
3H); 13C NMR (100 MHz, CDCl3) δ: 171.9, 136.5,
129.0, 120.9, 30.7, 9.5.
Typical procedure
Powder CBr4 (0.1 mmol) was added to the mixture
of acetophenone oxime 1a (1.0 mmol) and PPh3 (0.1
mmol) in toluene (1 mL), and heated it to 80 ℃ for 30
min. After removal of the solvent under reduced pres-
sure, N-phenylacetamide 2a was obtained by column
chromatography on silica gel [V(EtOAc)/V(PE)＝2/3] in
85% yield.
N-Phenylbutanamide (2m)[14] White solid (126
mg, 77%). 1H NMR (400 MHz, CDCl3) δ: 7.73 (br, 1H),
7.48－7.56 (m, 2H), 7.27 (t, J＝7.9 Hz, 2H), 7.02－
7.10 (m, 1H), 2.31 (t, J＝7.5 Hz, 2H), 1.68－1.77 (m,
2H), 0.96 (t, J＝7.4Hz, 3H); 13C NMR (100 MHz,
CDCl3) δ: 171.7, 138.0, 128.9, 124.2, 120.0, 39.5, 19.1,
13.7.
Characterization data for the products
N-Phenylhexanamide (2n)[14] White solid (151
N-Phenylacetamide (2a)[3b] White solid (115 mg,
85% yield). 1H NMR (400 MHz, CDCl3) δ: 7.48 (d, J＝
7.9 Hz, 2H), 7.30 (t, J＝7.9 Hz, 2H), 7.19 (br, 1H), 7.09
(t, J＝7.4 Hz, 1H), 2.16 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ: 129.0, 124.3, 119.8, 24.6.
1
mg, 79%). H NMR (400 MHz, CDCl3) δ: 7.50 (d, J＝
8.0 Hz, 1H), 7.42 (br, 1H), 7.28 (t, J＝7.9 Hz, 1H), 7.07
(t, J＝7.4 Hz, 1H), 2.33 (t, J＝7.6 Hz, 2H), 1.67－1.74
(m, 2H), 1.31－1.34 (m, 4H), 0.87－0.89 (m, 3H); 13C
NMR (100 MHz, CDCl3) δ: 171.6, 138.0, 128.9, 124.1,
119.8, 37.7, 31.4, 25.3, 22.4, 13.9.
N-o-Tolylacetamide (2d)[12] White solid (119 mg,
80% yield). 1H NMR (400 MHz, CDCl3) δ: 7.69 (d, J＝
7.9 Hz, 1H), 7.12－7.22 (m, 3H), 7.06 (t, J＝7.4 Hz,
1H), 2.23 (s, 3H), 2.17 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ: 168.5, 135.6, 130.4, 129.5, 126.7, 125.4,
123.6, 24.1, 17.8.
3,4-Dihydroquinolin-2(1H)-one (2o)[2h]
White
1
solid (94 mg, 64%). H NMR (400 MHz, CDCl3) δ:
8.78 (br, 1H), 7.09－7.22 (m, 2H), 6.97 (td, J＝7.5, 1.2
Hz, 1H), 6.80 (dd, J＝7.9, 1.2 Hz, 1H), 2.94－2.97 (m,
2H), 2.61－2.65 (m, 2H); 13C NMR (100 MHz, CDCl3)
δ: 172.0, 137.2, 127.9, 127.5, 123.6, 123.1, 115.4, 30.7,
25.3.
N-(4-Fluorophenyl)acetamide (2f)[12] White solid
1
(121 mg, 79% yield). H NMR (400 MHz, CDCl3) δ:
Azacyclotridecan-2-one (2q)[3b] White solid (85
mg, 43%). 1H NMR (400 MHz, CDCl3) δ: 5.44 (br, 1H),
3.26－3.31 (m, 2H), 2.12－2.27 (m, 2H), 1.60－1.69
(m, 2H), 1.46－1.51 (m, 2H), 1.22－1.40 (m, 14H); 13C
NMR (100 MHz, CDCl3) δ: 173.3, 39.0, 37.0, 28.3,
26.7, 26.3, 26.2, 25.7, 25.2, 24.9, 24.7, 23.9.
7.31－7.76 (m, 2H), 7.14 (br, 1H), 6.99 (t, J＝8.7 Hz,
2H), 2.15 (s, 3H); 13C NMR (100 MHz, CDCl3) δ: 168.1,
159.4 (d, J＝244 Hz), 133.8 (d, J＝2.5 Hz), 121.7 (d,
J＝7.8 Hz), 115.6 (d, J＝22.5 Hz), 24.4.
N-(4-Chlorophenyl)acetamide (2g)[12] White sol-
id (127 mg, 75% yield). 1H NMR (400 MHz, CDCl3) δ:
2
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Chin. J. Chem. 2017, XX, 1—5

Beckmann Rearrangement of Ketoximes for Synthesis of Amides
Results and Discussion
then turned to investigating the scope of ketoximes. As
shown Scheme 2, a wide range of ketoximes exhibited
high reactivities, and the corresponding amides were
obtained in moderate to good yields through an aryl
group migration. Aryl ketoximes bearing electron do-
nating groups (Me or MeO) in the phenyl ring were all
smoothly converted into the corresponding amides in
yields ranging from 80% to 87% in a short reaction pe-
riod (2b－2e). No significant steric effect was observed
by employing phenyl ketoximes with para-, meta-, or
ortho-methyl in the phenyl ring as substrates, and cor-
responding amides 2b, 2c and 2d were isolated in 83%,
81% and 80% yields, respectively. A longer reaction
time was needed for aryl ketoximes bearing electron
withdrawing groups (－halo and －CF3) in the phenyl
ring (2f－2i). Aryl ketoximes with a long alkyl chain,
such as propiophenone oximes 1g－1l, butyrophenone
oxime 1m, and hexanophenone oxime 1n were used as
substrates in the reaction. To our delight, the corre-
sponding products (2g－2n) were obtained in 77%－
83% yields. In the cases of a benzocycloketoxime 1o,
the desired product 2o was delivered in 64%. Unfortu-
nately, aliphatic cycloketoxime 1p was not viable for
this protocol. Then, aliphatic macrocyclic ketoxime 1q
and acyclic aliphatic ketoxime 1r were tested under the
optimized condition. The desired product 2q was pro-
duced in 43% yield, however, only trace amount of 2r
was detected.
We commenced to examine the Beckmann rear-
rangement of acetophenone oxime 1a with 10 mol% of
carbon tetrabromide and 10% triphenylphosphine in
CH3CN at 80 ℃ under nitrogen atmosphere for 1 h. As
a result, the desired N-phenylacetamide 2a could be
formed in 19% yield (Table 1, entry 1). In order to im-
prove the yield of 2a, DCE, CH3OH, THF and toluene
were also tested as solvents (Table 1, entries 2－4).
When the reaction was carried out in toluene, the yield
of 2a could be increased to 85%. Other halides, such as
CHBr3, CH2Br2 and CCl4, were less efficient and gave
inferior yields of 2a (Table 1, entries 5－7). Among al-
ternative tertiary phosphines investigated, P(OEt)3 and
triphenylphosphine-m-sulfonate (TPPMS) were inactive
with only trace amounts of the product detected, while
tricyclohexyl phosphine (TCHP) afforded a moderate
yield (Table 1, entries 8－10). Furthermore, the yield of
product could not be improved by further variation of
the reaction temperature (Table 1, entries 11 and 12).
Thus, the optimized conditions to be 1 mmol of 1a with
10 mol% of carbon tetrabromide, 10 mol% of tri-
phenylphosphine in toluene at 80 ℃ for 0.5 h under
nitrogen atmosphere.
Table 1 Optimization of the reaction conditionsa
Scheme 2 Substrate scope
OH
H
N
10 mol% CBr4
10 mol% PPh3
N
O
R
Tertiary
phosphine
Conversionc/
%
Entry Halide
Solvent
Yieldb/%
R
R1
toluene, 80 oC, N2
R1
1
2
CBr4
CBr4
CBr4
CBr4
CBr4
CHBr3
CH2Br2
CCl4
PPh3
PPh3
PPh3
PPh3
PPh3
PPh3
PPh3
PPh3
CH3CN
DCE
28
55
93
0
19
48
2
1
H
H
3
toluene
CH3OH
THF
85
N
N
R
4
trace
trace
trace
trace
9
O
O
5
4
R = H, 2a, 0.5 h, 85%
R = 4-Me, 2b, 0.5 h, 83%
R = 3-Me, 2c, 0.5 h, 81%
R = 2-Me, 2d, 0.5 h, 80%
R = 4-OMe, 2e, 0.5 h, 87%
R = 4-F, 2f, 1 h, 79%
R = 4-Cl, 2g, 1 h, 75%
R = 4-Br, 2h, 2 h, 68%
R = 4-CF3, 2i, 2 h, 51%
2n, 0.5 h, 79%
6
toluene
toluene
toluene
0
H
N
O
7
0
8
21
0
9
CBr4
CBr4
CBr4
CBr4
CBr4
P(OEt)3 toluene
TPPMS toluene
trace
trace
45
58d
83e
2o, 0.5 h, 64%
10
11
12
13
0
NH
O
TCHP
PPh3
toluene
toluene
toluene
50
64
93
H
N
2p, 2 h, trace
PPh3
R
O
a Reaction conditions: 1a (1.0 mmol), halide (0.1 mmol), tertiary
phosphine (0.1 mmol) in solvent (1 mL) at 80 ℃ for 0.5 h under
nitrogen atmosphere; b Isolated yield; Conversion (%) of aceto-
phenone oxime as determined by GC analysis with tridecane as
an internal standard; d Reaction performed at 60 ℃; e Reaction
performed at 100 ℃.
H
N
O
R = H, 2j, 0.5 h, 83%
R = 4-Me, 2k, 0.5 h, 78%
R = 4-Cl, 2l, 1 h, 71%
c
2q, 2 h, 43%
H
N
O
N
O
H
With the optimized conditions in hand, our attention
2r, 2 h, trace
2m, 0.5 h, 77%
Chin. J. Chem. 2017, XX, 1—5
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3

Gao & Bai
COMMUNICATION
Scheme 3 Possible mechanism
OH
N
Ph
H
N
1a
Ph
O
Br
PPh3
+
CBr4
2a
PPh3
CBr3
OH
N
A
H
N
Ph
N
Ph
Ph
OH
1a
N OH Br
PPh3
O
Ph
N
Ph
N
HO PPh3
CBr3
CBr3
F
Ph
B
D
E
C
O PPh3
CHBr3
According to previous reports,[4a-4e] catalytic
amounts of hydrogen halide (HBr or HCl) played a key
role in the organocatalytic Beckmann rearrangement. To
confirm the influence of an acidic intermediate on the
reaction, 10 mol% of K2CO3, Et3N or H2O was added in
the model reaction, and the Beckmann rearrangement of
1a was found to be inhibited. The results indicated that
an acidic intermediate might be formed in the reaction
process. Based on the experimental results, and Lambert
and Deng’s reports,[2o,4e,4g,4h] a possible mechanism is
proposed using 1a as an example (Scheme 3). Nucleo-
philic attack of PPh3 on CBr4 forms salt A,[8-10,12] which
reacts with 1a giving the intermediate B. Intermolecular
migration of phenyl group releases C to form D. Then,
the reaction is proceeded following a nitrilium cation D
catalyzed self-propagating mechanism.[4g,4h] Reaction of
D with a second molecular of 1a affords E. Migration of
phenyl group gives E regenerates D and produces F,
which is in resonance with the final product 2a.
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Conclusions
In summary, we have developed an efficient method
for the Beckmann rearrangement using catalytic
amounts of carbon tetrabromide and triphenylphosphine
as a catalyst under mild conditions. Good yields of
products, inexpensive and readily available reagents
make this procedure a promising alternative for the am-
ides synthesis. Further mechanistic studies and applica-
tions of this method are in progress.
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Acknowledgement
We thank Shaanxi Provincial Key Laboratory Project
(15JS004) and Baoji University of Arts and Sciences
(ZK15046) for financially supporting this work.
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