Oxidation of Tertiary Aromatic Alcohols to Ketones in Water

Article abstract of DOI:10.1002/adsc.201800612

A new rosin-based amphiphile enables the oxidation of tertiary aromatic alcohols in water under mild conditions. The oxidation process is mediated by β-scission of alkoxy radicals. Our catalyst system including the surfactant, catalysts, and water can be easily recycled within the same reaction vial. (Figure presented.).

Full text of DOI:10.1002/adsc.201800612

Title: Oxidation of Tertiary Aromatic Alcohols to Ketones in Water
Authors: Dengfeng Chen, Yuchen Zhang, Xingyu Pan, Fei Wang, and
Shenlin Huang
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10.1002/adsc.201800612
Advanced Synthesis & Catalysis
UPDATE
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Oxidation of Tertiary Aromatic Alcohols to Ketones in Water
Dengfeng Chen,a Yuchen Zhang,a Xingyu Pan,b Fei Wang,a and Shenlin Huang a*
a
Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, College of Chemical
Engineering, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, Jiangsu Co-Innovation Center of
Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing, 210037, P. R. China
E-mail: shuang@njfu.edu.cn
b
Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract. A new rosin-based amphiphile enables the
oxidation of tertiary aromatic alcohols in water under mild
conditions. The oxidation process is mediated by β-scission
of alkoxy radicals. Our catalyst system including the
surfactant, catalysts, and water can be easily recycled within
the same reaction vial.
Keywords: Green chemistry; Micellar catalysis; Water
chemistry; Rosin; Oxidation
which avoids some potential health, safety, and
environmental issues caused by organic solvents.[8]
Introduction
The oxidation of alcohols to carbonyl compounds is
among the most important oxidations in organic
chemistry. While numerous reagents and methods are
available for converting primary alcohols to
aldehydes and secondary alcohols to ketones,[1]
tertiary alcohols are generally considered to be
unaffected under these conditions in textbooks on
basic organic chemistry. Indeed, the oxidation of
tertiary alcohols to ketones has scarcely been
investigated so far,[2] and is mainly limited to specific
substrates, such as allylic alcohols, diols, and strained
cyclic alcohols. In principle, ketones can be obtained
from tertiary alcohols through the cleavage of
adjacent C–C bonds, including β-carbon elimination
(Scheme 1a)[3] and β-scission (Scheme 1b).[4] So far,
both β-carbon elimination and β-scission strategies
have been used mainly to access organometallic
species[5] or alkyl radicals[6] for further
transformations in catalysis, along with ketone
byproducts.
Recently, Knowles reported a novel photocatalytic
method for the oxidation of tertiary alcohols to
ketones in dichloromethane (Scheme 1c).[7] However,
this β-scission reaction only applies to tertiary
alcohols with an activated arene like PMP (p-
methoxyphenyl), limiting the applicability of this
elegant methodology. Herein, we present the design,
synthesis, and application of rosin-based amphiphiles
as a new class of “designer” surfactants, enabling the
first general oxidation of tertiary aromatic alcohols to
ketones via β-scission in water (Scheme 1d). These
reactions proceed under aqueous reaction medium,
Scheme 1. Oxidation of Tertiary Alcohols to Ketones
Results and Discussion
Initially, we started our investigation with 2-
phenylpropan-2-ol 1 as a model substrate, using a
catalytic amount of silver nitrate (AgNO3) together
with
a
stoichiometric amount of potassium
peroxodisulfate (K2S2O8) to generate alkoxyl
radicals.[6a,9] The reaction did not take place in dry
organic solvent (Table 1, entries 1 and 2). We were
delighted to find that the desired oxidation reaction
was feasible in organic solvent/water or pure water,
albeit in low yields (Table 1, entries 3 to 5). As our
continuing efforts exploring sustainable synthetic
methodology in water,[10] we further evaluated this
1
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10.1002/adsc.201800612
Advanced Synthesis & Catalysis
oxidation in aqueous micellar medium. To our delight, dehydroabietinol-polyethyleneglycol-succinate
in the presence of TPGS-750-M, a “benign-by-design” monomethyl ethers (DAPGS) were prepared in two
amphiphile developed by Lipshutz,[11] acetophenone
could indeed be obtained in a higher yield in water at
30 °C (Table 1, entry 6), while other surfactants
afforded inferior results (Table 1, entries 7 and 8). A
survey of reaction concentration and additives
revealed that Bi(OTf)3 is the preferred Lewis acid,
providing the desired acetophenone oxidation product
in a promising yield of 75% (Table 1, entry 11).
However, the yield could not be improved further
using TPGS-750-M by varying different silver salts,
Lewis acids, and oxidants (see the Supporting
Information). These results encouraged us to design
more suitable amphiphiles for this transformation.
steps (see SI). We envisioned that DAPGS bearing a
rigid inner core, dehydroabietinol without any long
aliphatic chain compared to TPGS-750-M and other
surfactants, would produce micelles with different
shape, size, and distribution, which was comfirmed
by cryogenic transmission electron microscopy (cryo-
TEM, Figure 1) and dynamic light scattering (DLS)
experiments (for more details, see SI). Notably,
extensive aggregation of nanomicelles was observed,
which might facilitate the exchange process.[15] After
the addition of AgNO3/K2S2O8/Bi(OTf)3, particle size
went up from 12 nm to 58 nm. Benevolently,
DAPGS-750-M indeed gave acetophenone in
excellent yield at 30 °C (Table 1, entry 14),
suggesting that micellar catalysis might be playing a
pivotal role in this transformation. Finally, removing
Bi(OTf)3 from the reaction led to a significantly
lower yield (Table 1, entry 15), indicating there might
be some co-effect Bi(OTf)3 and DAPGS-750-M
which requires further experiments to clarify.
Table 1. Optimization of the Reaction Conditions[a]
Entry Additive Solvent
Yield[b]
1
2
3
4
5
6
7
8
None
None
None
None
None
None
None
None
None
None
DCM[c]
0%
0%
Figure 1. Cryo-TEM images of 2 wt% DAPGS-750-M
MeCN[c]
DCM/H2O = 1/1[c]
Acetone/ H2O = 1/1[c]
H2O[c]
19%
23%
25%
35%
27%
29%
31%
37%
75%
38%
43%
90%
38%
We next explored the substrate scope of tertiary
alcohols under the optimized conditions (Table 2).
Model substrate 1 could be oxidized in 88% isolated
yield. A high yield (90%) was obtained from the 10
mmol scale oxidation of 1, as the stirring is much
more efficient for large-scale reactions. Bromo-
substituted benzylic alcohols such as 2-(2-
TPGS-750-M/H2O[c]
Brij L23/H2O[c]
Tween 80/H2O[c]
TPGS-750-M/H2O[d]
TPGS-750-M/H2O[e]
9
10
11
12
13
14
Bi(OTf)3 TPGS-750-M/H2O[e]
bromophenyl)propan-2-ol
bromophenyl)propan-2-ol
(2),
2-(3-
2-(4-
ZnCl2
FeCl3
TPGS-750-M/H2O[e]
TPGS-750-M/H2O[e]
(3),
and
bromophenyl)propan-2-ol (4) proceeded smoothly
under the standard conditions, regardless of the
location of the substituent, suggesting that steric
effects had little influence on the oxidation. Other
halogen-substituted benzylic alcohols (5–7) gave
71%, 89%, and 48% yields respectively, thus
demonstrating the tolerance of halogens and the
potentiality of further functionalization. In addition,
aromatic tertiary alcohols with electron-withdrawing
substituents (8-10) worked equally well as those with
electron-donating groups (11 and 12). To our delight,
heterocycles like 2-(thiophen-2-yl)propan-2-ol (13)
and 2-(pyridin-2-yl)propan-2-ol (14) were also
oxidized smoothly, leading to the desired 1-
Bi(OTf)3 DAPGS-750-M/H2O[e]
15
None
DAPGS-750-M/H2O[e]
[a]
Conditions: 1 (0.3 mmol), AgNO3 (3 mol%), K2S2O8
(0.9 mmol), Bi(OTf)3 (3 mol%), solvent (0.5 M), at 30 °C
for 24 h. [b] Yields were determined by HPLC analysis with
1-nitrobenzene as an internal standard. [c] 0.1 M. [d] 0.25 M.
[e]
0.5M. Brij L23 = polyoxyethylene (23) lauryl ether.
Tween 80 = polysorbate 80.
Given the superb activity of TPGS-750-M in
micellar catalysis,[12,13] we were curious to explore if
the structurally similar amphiphiles derived from
dehydroabietinol would be suitable alternatives. The
lipophilic dehydroabietinol portion can be easily
obtained from renewable dehydroabietic acid，one of
the important resin acids in rosin[14] with an annual
production of more than one million metric tons.
Following a modified procedure based on Lipshutz’s
(thiophen-2-yl)ethan-1-one
and
1-(pyridin-2-
yl)ethan-1-one respectively in moderate yield.
Unsymmetrical diaryl alcohol (15) were also
competent in the optimized conditions. Unfortunately,
2-(4-aminophenyl)propan-2-ol (16), bearing an free
amine (NH2), was not compatible with this reaction.
preparation
of
TPGS-750-M,[11c]
several
2
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10.1002/adsc.201800612
Advanced Synthesis & Catalysis
Table 2. Scope of Tertiary Alcohols[a,b]
Table 3. Further Scope of Tertiary Alcohols[a,b]
[a]
Conditions: alcohol (0.3 mmol), AgNO3 (3 mol%),
K2S2O8 (0.9 mmol), Bi(OTf)3 (3 mol%), 2 wt% DAPGS-
750-M/H2O (0.5 M) at 30 °C for 24 h. [b] Isolated yields.
[a]
Conditions: alcohol (0.3 mmol), AgNO3 (3 mol%),
Afterward, we
performed
some
control
K2S2O8 (0.9 mmol), Bi(OTf)3 (3 mol%), 2 wt% DAPGS-
750-M/H2O (0.5 M) at 30 °C for 24 h. [b] Isolated yields. [c]
10 mmol scale. [d] 36 h.
experiments to elucidate the reaction mechanism.
Control experiments confirmed the requirement of
both silver nitrate (AgNO3) and potassium
peroxodisulfate (K2S2O8) to generate the alkoxyl
radical (Scheme 2a). Moreover, α-methylstyrene was
not detected, which might rule out the possibility of a
hydration step in the process. A radical pathway was
further confirmed by conducting the radical inhibition
experiment with radical scavenger TEMPO (Scheme
2b). Moreover, a set of Lewis acids including BiX3,
M(OTf)3, and HOTf were examined (see the SI,
Table S2) to probe the role of Bi(OTf)3 indicating
both Bi3+ and TfO- are important for the reaction. All
of them showed inferior reaction efficiency. Lastly,
Furthermore, we have examined tertiary
arylcarbinols bearing different alkyl, alkenyl, or
alkynyl groups (Table 3, 17–28). Gratifyingly,
various lengths of alkyl chains showed good
reactivities under the optimal conditions. Notably,
neither C–phenyl bond cleavage nor C–methyl bond
cleavage was observed (17–22). This highly selective
C–C bond cleavage pathway is strongly suggestive of
a β-scission mechanism instead of a β-carbon
elimination process, as β-scission generally prefers
elimination of the most stable possible alkyl
radical.[4c,d] Interestingly, 2-phenylbut-3-en-2-ol (23)
and 2-phenylbut-3-yn-2-ol (24) underwent exclusive
C–vinyl and C–alkynyl bond cleavages respectively.
The same selectivity was observed when 3-
phenylpent-1-en-3-ol (25) and 3-phenylpent-1-yn-3-
ol (26) were examined under the standard
conditions.[16] Remarkably, tertiary carbinols without
Me substituents (27–30) successfully furnished the
desired oxidation products, releasing the most stable
alkyl radical.
2-hydroxy-1,2-diphenylpropan-1-one
31
was
subjected to the standard reaction conditions,
delivering acetophenone (48% yield) and benzoic
acid (30% yield) along with 50% recovery of starting
material (Scheme 2c). These collectively suggest that
bismuth triflate/alcohol complex A may be generated
first. A facile Bi–O bond homolysis[17] subsequently
would provide alkoxyl radical B. The alkoxyl radical
B then undergoes β-scission to yield acetophenone
and carbonyl radical C, which is further oxidized to
benzoic acid.
3
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10.1002/adsc.201800612
Advanced Synthesis & Catalysis
flask recycling of the DAPGS surfactant, catalyst and
water. Further applications of our new surfactant and
variations will be published in due course.
Experimental Section
General procedure for oxidation of tertiary alcohols:
A Nitrogen flashed vial was charged with AgNO3 (1.6 mg,
3 mol%), Bi(OTf)3 (6 mg, 3 mol%) and K2S2O8 (245.8 mg,
3 eq), followed with 2 wt% DAPGS-750-M/H2O (0.6 mL,
0.5 M) and alcohol (0.3 mmol). The solution was stirred at
30 °C until completed. The solution was then exacted with
EtOAc, dried over anhydrous Na2SO4, concentrated under
reduced pressure. The crude mixture was purified by flash
column chromatography (5% to 10% ethyl acetate in
petroleum ether) to afford desired products.
Acknowledgements
Financial support provided by the Natural Science Foundation of
China (21502094), and the Natural Science Key Project of the
Jiangsu Higher Education Institutions (17KJA220003) is warmly
acknowledged. We are also grateful for support by the Top-notch
Academic Programs Project of Jiangsu Higher Education
Institutions (TAPP), the Priority Academic Program
Development of Jiangsu Higher Education Institutions (PAPD),
the Doctorate Fellowship Foundation of Nanjing Forestry
University, and advanced analysis and testing center of Nanjing
Forestry University.
Scheme 2. Mechanistic Investigations
To further assess the sustainability of this general
methodology, we investigated in-flask recycling
experiments. Once an oxidation is complete, the
desired ketone product is extracted from the aqueous
medium with minimal amounts of EtOAc. To the
remaining aqueous mixture is then introduced
arylcarbinol 4 and K2S2O8, leading to another
oxidation. As shown in Table 4, the reaction
efficiency remained almost the same for three cycles,
resulting in a low E factor[18] of 11.
References
[1] a) G. Tojo, M. Fernandez, Eds. Oxidation of Alcohols
to Aldehydes and Ketones. In Basic Reactions in
Organic Synthesis, Springer, New York, 2010; b) K. C.
Miles, S. S. Stahl, Aldrichimica Acta 2015, 48, 8; c) B.
L. Ryland, S. S. Stahl, Angew. Chem. 2014, 126, 8968;
Angew. Chem., Int. Ed. 2014, 53, 8824.
Table 4. E Factors and Recycling Study[a,b]
[2] K. Wietzerbin, J. Bernadou, B. Meunier, Eur. J. Inorg.
Chem. 2000, 7, 1391, and references cited therein.
[3] a) M. Miura, T. Satoh In Palladium in Organic
Synthesis, Vol. 14 (Ed.: J. Tsuji), Springer, Berlin, 2005,
pp. 1−20; b) M. Murakami, M. Makino, S. Ashida, T.
Matsuda, Bull. Chem. Soc. Jpn. 2006, 79, 1315; c) N.
Cramer, T. Seiser, Synlett 2011, 4, 449; d) G.
Fumagalli, S. Stanton, J. F. Bower, Chem. Rev. 2017,
117, 9404.
[a]
Conditions: alcohol (0.3 mmol), AgNO3 (3 mol%),
[4] a) L. Feray, N. Kuznetsov, P. Renaud Radicals in
Organic Synthesis; Vol. 2 (Eds.: P. Renaud, M. P. Sibi),
Wiley-VCH, Weinheim, 2001, pp. 246−278; b) E.
Suꢀrez, M. S. Rodriguez Radicals in Organic Synthesis;
Vol. 2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH,
Weinheim, 2001, pp. 440−454; c) M. Salamone, M.
Bietti, Synlett 2014, 25, 1803; d) M. Murakami, N.
Ishida, Chem. Lett. 2017, 46, 1692.
K2S2O8 (0.9 mmol), Bi(OTf)3 (3 mol%), 2 wt% DAPGS-
750-M/H2O (0.5 M) at 30 °C for 24 h. [b] Isolated yields.
Conclusion
In summary, we have introduced a new rosin-based
surfactant DAPGS-750-M, which enabled a general
oxidation of tertiary aromatic alcohols to ketones in
water. A variety of tertiary arylcarbinols can be
oxidized to ketones in good to high yields. In addition,
our surfactant would be complementary to the well-
known TPGS-750-M and others used in micellar
catalysis. Notably, this oxidation methodology
utilizes an aqueous reaction medium, allowing for in-
[5] For selected recent examples, see: a) G. Smits, B.
Audic, M. D. Wodrich, C. Corminboeuf, N. Cramer,
Chem. Sci. 2017, 8, 7174; b) E. Ozkal, B. Cacherat, B.
Morandi, ACS Catal. 2015, 5, 6458; c) N. Ishida, D.
Neꢁas, Y. Masuda, M. Murakami, Angew. Chem. 2015,
127, 7526; Angew. Chem., Int. Ed. 2015, 54, 7418; d) L.
Souillart, N. Cramer, Chem. Sci. 2014, 5, 837; e) J.
4
This article is protected by copyright. All rights reserved.

10.1002/adsc.201800612
Advanced Synthesis & Catalysis
Wang, W. Chen, S. Zuo, L. Liu, X. Zhang, J. Wang,
[12] For selected recent examples, see: a) N. A. Isley, F.
Gallou, B. H. Lipshutz, J. Am. Chem. Soc. 2013, 135,
17707; b) B. H. Lipshutz, S. Ghorai, Green Chem.
2014, 16, 3660; c) S. Handa, Y. Wang, F. Gallou, B. H.
Lipshutz, Science 2015, 349, 1087; d) J. Feng, S.
Handa, F. Gallou, B. H. Lipshutz, Angew. Chem. 2016,
128, 9125; Angew. Chem., Int. Ed. 2016, 55, 8979; e) S.
Handa, M. P. Andersson, F. Gallou, J. Reilly, B. H.
Lipshutz, Angew. Chem. 2016, 128, 4998; Angew.
Chem., Int. Ed. 2016, 55, 4914; f) N. A. Isley, Y. Wang,
F. Gallou, S. Handa, D. H. Aue, B. H. Lipshutz, ACS
Catal. 2017, 7, 8331.
Angew. Chem. 2012, 124, 12500; Angew. Chem., Int.
Ed. 2012, 51, 12334; f) Z.-Q. Lei, F. Pan, H. Li, Y. Li,
X.-S. Zhang, K. Chen, X. Wang, Y.-X. Li, J. Sun, Z.-J.
Shi, J. Am. Chem. Soc. 2015, 137, 5012; g) M. Sai, H.
Yorimitsu, K. Oshima, Angew. Chem. 2011, 123, 3352;
Angew. Chem., Int. Ed. 2011, 50, 3294.
[6] For selected recent examples, see: a) S. Chiba, Z. Cao,
S. A. A. El Bialy, K. Narasaka, Chem. Lett. 2006, 35,
18; b) H. Zhao, X. Fan, J. Yu, C. Zhu, J. Am. Chem.
Soc. 2015, 137, 3490; c) S. Ren, C. Feng, T.-P. Loh,
Org. Biomol. Chem. 2015, 13, 5105; d) K. Jia, F. Zhang,
H. Huang, Y. Chen, J. Am. Chem. Soc. 2016, 138, 1514; [13] For a related surfactant FI-750-M: a) J. Brals, J. D.
e) J.-J. Guo, A. Hu, Y. Chen, J. Sun, H. Tang, Z. Zuo,
Angew. Chem. 2016, 128, 15545; Angew. Chem., Int.
Ed. 2016, 55, 15319.
Smith, F. Ibrahim, F. Gallou, S. Handa, ACS Catal.
2017, 7, 7245; b) J. D. Smith, T. N. Ansari, M. P.
Andersson, D. Yadagiri, F. Ibrahim, S. Liang, G. B.
Hammond, F. Gallou, S. Handa, S. Green Chem. 2018,
20, 1784; c) L. Finck, J. Brals, B. Pavuluri, F. Gallou, S.
[7] H. G. Yayla, H. Wang, K. T. Tarantino, H. S. Orbe, R.
R. Knowles, J. Am. Chem. Soc. 2016, 138, 10794.
Handa.
J.
Org.
Chem.
ASAP,
DOI:
10.1021/acs.joc.7b03143.
[8] a) T. Laird, Org. Process Res. Dev. 2012, 16, 1; b) P. J.
Dunn Pharmaceutical Process Development; (Eds.: J.
A. Blacker, M. T. Williams), Royal Society of
Chemistry, London, 2011, Chapter 6; c) C. Jimenez-
Gonzales, D. J. Constable, Eds. Green Chemistry and
Engineering: A Practical Approach, Wiley, New York,
2011; d) D. Prat, A. Wells, J. Hayler, H. Sneddon, C. R.
McElroy, S. Abou-Shehada, P. J. Dunn, Green Chem.
2016, 18, 288; e) B. H. Lipshutz, F. Gallou, S. Handa,
ACS Sustainable Chem. Eng. 2016, 4, 5838; f) B. H.
Lipshutz, J. Org. Chem. 2017, 82, 2806.
[14] a) P. A. Wilbon, F. Chu, C. Tang, Macromol. Rapid
Commun. 2013, 34, 8; b) K. Yao, C. Tang,
Macromolecules 2013, 46, 1689; c) K. Yao, J. Wang,
W. Zhang, J. S. Lee, C. Wang, F. Chu, X. He, C. Tang,
Biomacromolecules 2011, 12, 2171.
[15] J. D. Smith, T. N. Ansari, M. P. Andersson, D.
Yadagiri, F. Ibrahim, S. Liang, G. B. Hammond, F.
Gallou, S. Handa, Green Chem. 2018, Advance Article,
DOI: 10.1039/c7gc03514d.
[9] a) R. G. R. Bacon, J. R. Doggart, J. Chem. Soc. 1960,
1332; b) F. P. Greenspan, H. M. Woodburn, J. Am.
Chem. Soc. 1954, 76, 6345; c) M. Hirano, K. Kojima, S.
Yakabe, T. Morimoto, J. Chem. Res. (S) 2001, 274; d)
S. Chiba, Z. Cao, S. A. A. El Bialy, K. Narasaka, Chem.
Lett. 2006, 35, 18; e) A. Ilangovan, S. Saravanakumar,
S. Malayappasamy, Org. Lett. 2013, 15, 4968; f) S.-C.
Lu, H.-S. Li, S. Xu, G.-Y. Duan, Org. Biomol. Chem.
2017, 15, 324; g) J. Yu, H. Zhao, S. Liang, X. Bao, C.
Zhu, Org. Biomol. Chem. 2015, 13, 7924.
[16] It seems that the proposed radical mechanism does not
apply to these cases, as the vinyl and alkynyl radicals
are less stable than alkyl radicals.
[17] I. J. Casely, J. W. Ziller, M. Fang, F. Furche, W. J.
Evans,J. Am. Chem. Soc. 2011, 133, 5244.
[18] a) R. A. Sheldon, Green Chem. 2007, 9, 1273; b) R. A.
Sheldon, I. W. C. E. Arends, U. Hanefeld, Eds. Green
Chemistry and Catalysis, Wiley-VCH, Weinheim, 2007;
c) B. H. Lipshutz, N. A. Isley, J. C. Fennewald, E. D.
Slack, Angew. Chem. 2013, 125, 11156; Angew. Chem.,
Int. Ed. 2013, 52, 10952, and references cited therein; d)
F. Roschangar, R. A. Sheldon, C. H. Senanayake,
Green Chem. 2015, 17, 752.
[10] D. Chen, Q. Feng, Y. Yang, X.-M. Cai, F. Wang, S.
Huang, Chem. Sci. 2017, 8, 1601.
[11] a) B. H. Lipshutz, S. Ghorai, Aldrichimica Acta 2012,
45, 3; b) B. H. Lipshutz, S. Ghorai, Aldrichimica Acta
2008, 41, 59; c) B. H. Lipshutz, S. Ghorai, A. R. Abela,
R. Moser, T. Nishikata, C. Duplais, A. Krasovskiy, R.
D. Gaston, R. C. Gadwood, J. Org. Chem. 2011, 76,
4379.
5
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10.1002/adsc.201800612
Advanced Synthesis & Catalysis
UPDATE
Oxidation of Tertiary Aromatic Alcohols to
Ketones in Water
Adv. Synth. Catal. Year, Volume, Page – Page
Dengfeng Chen, Yuchen Zhang, Xingyu Pan, Fei
Wang, and Shenlin Huang*
6
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