A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls

Article abstract of DOI:10.1039/d0ob00406e

A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.

Full text of DOI:10.1039/d0ob00406e

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One-pot protocol for the fluorosulfonation and Suzuki coupling of
phenols and bromophenols, streamlined access to biaryls and
terphenyls
Received 00th January 20xx,
Accepted 00th January 20xx
Xinmin Li,*a Tingting Zhang,a Rui Hu,a Hang Zhang,a Changyue Ren,a Zeli Yuan*a
DOI: 10.1039/x0xx00000x
www.rsc.org/
One-pot protocol for the fluorosulfation of and Suzuki coupling fluorosulfates mediated Suzuki–Miyaura reaction has been reported
16
phenols reaction is described. The tandem reaction proceeds by several groups,15,
the one-pot tandem reaction of
efficiently at room temperature, and various of biaryls and biaryl fluorosulfation and Suzuki coupling reaction from phenols was rare.
fluorosulfates were obtained in good to excellent yields. In 2015, Hanley et al. reported conversion of phenols to the
Furthermore, biaryl fluorosulfate were utilized as versatile building corresponding biaryl by in situ activation with SO2F2.17 This strategy
blocks for the preparation of terphenyls.
merged phenol activation and subsequent cross-coupling into a
single operation, but phosphine ligand and long reaction time were
The construction of carbon–carbon bonds is a fundamental task in required in the cross-coupling reaction. Recently, our group reported
the synthesis of organic compounds.1 There is little doubt that the a practical protocol for the Suzuki–Miyaura reaction of aryl
Suzuki-Miyaura cross-coupling reaction has become one of the most fluorosulfates and various arylboron compounds in EtOH/H2O at 80
powerful methodologies for building up carbon–carbon and biaryls.2- oC.18 During these studies, it was found that aryl fluorosulfates could
4 The Suzuki-Miyaura reaction is generally green and easy to perform be obtained nearly quantitative yield by treating phenols with SO2F2
due to the mild reaction conditions, low toxicity associated with under basic condition. Based on these findings, we decided to further
6
boron compounds and broad functional-group tolerance.5, Aryl investigate the use of phenols for the synthesis of biaryls directly. We
halides are useful electrophiles for the Suzuki-Miyaura reaction.7-9 report herein the one-pot protocol for the synthesis of biaryls and
However, the additional steps to pre-synthesize aryl halides and the biaryl fluorosulfates. Highlighted features of this strategy are (a)
stoichiometric quantity of halide waste generated from the cross- telescoping the preparation of fluorosulfates and Suzuki coupling
coupling reaction, which limits their application in industry. Hence, into a one-pot operation. (b) no phosphine ligand needed; (c)
the development of more naturally abundant alternatives as reaction proceed under room temperature and air atmosphere; (d)
aromatic feedstocks is highly desirable.
aqueous solvent as reaction media.
Phenols, being readily available from naturally abundant lignins
and widely obtainable at very low cost from coal and cumene
industrial processes, are considered to be an attractive biorenewable
feedstock for synthesis.10, 11 However, the C−O bond of phenols has
a high dissociation energy, it is necessary to transform into more
active precursors (e.g., sulfonates, esters, carbamates, ethers, and
2. Results and discussion
At the outset of this study, we investigated the one-pot cross-
coupling of 4-hydroxybenzonitrile with phenylboronic acids at room
temperature. First, 4-hydroxybenzonitrile and Et3N were mixed in a
tube with a SO2F2 balloon at room temperature for 4 hours, then
phenylboronic acid, Et3N and 1 mol% Pd catalyst were added to the
mixture for another 10 hours. As shown in table 1, the base- or
catalyst-free did not lead to any 4-carbonitrilebiphenyl product
(Table 1, entries 1 and 7), suggesting that base and catalyst are
indispensable in this reaction system. Later reaction optimizations
showed that the amount of base has a significant affect to this one-
pot reaction. Only low yield of 4-carbonitrilebiphenyl was observed
by using 3.0 equiv of Et3N in this one-pot reaction (Table 1, entries 2
and 3). While adding 3.0 equiv of Et3N for each step, this one-pot
reaction afforded an 84% yield for the corresponding product (Table
metal salts) for various cross-coupling reactions.12 Such
a
preparatory process limits their efficiency for overall yields and step
economy. In recent years, several direct cross-coupling reactions
have been reported by the in situ activation of phenols through the
formation of inorganic salts,13 pivalate esters,14 et al. Although aryl
a. School of Pharmacy, Zunyi Medical University, Zunyi, China, E-mail:
Lixm@zmu.edu.cn
†Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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1, entry 4). Increasing the amount of base to 5.0 equiv for the first different site also worked well in this reaction, 4-methyl, 3-methyl,
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DOI: 10.1039/D0OB00406E
step, 4-carbonitrilebiphenyl was obtained with a similar yield (Table 2-methyl, 4-ethyl, boronic acids all produced the desired products
1, entries 5 and 6). Besides, PdCl2, Pd/C were also examined for this
reaction, however, the results were unsatisfied (Table 1, entries 8
and 9). Lower loading of Pd(OAc)2 to 0.5 mol%, only a 62% yield was
obtained (Table 1, entry 10). Thus, the optimized reaction conditions
for this one-pot coupling reaction are 3.0 equiv of Et3N with a SO2F2
balloon, 25 oC, 4 hours in EtOH/H2O (2 mL/2 mL) followed by addition
of boronic acid (1.2 equiv), 1 mol% Pd(OAc)2 and 3.0 equiv of Et3N for
10 hours.
Table 2 Substrate scope of phenols and arylboronic acidsa
R2
OH
SO2F2,
(1)
(2)
R1
R1
Pd(OAc)2
B(OH)2
R2
O
H3CO
R1
Table 1 Optimization of reaction conditions for one-pot synthesis of biaryl
R2
R2
compoundsa
R1 = 4-CN, 84%, 2a
4-NO2, 82%, 2b
4-CHO, 83%, 2c
4-COCH3, 95%, 2d
4-OCH3, 81%, 2e
4-CH3, 82%, 2f
R2 = 4-CHO, 94%, 2m
4-F, 90%, 2n
R2
=
4-CH3,83%, 2t
3-CH3,78%, 2u
B(OH)2
4-Cl, 93%, 2o
4-CH3, 90%, 2p
3-CH3, 91%, 2q
OH
SO2F2, Et3N
3,5-(CH3)2, 88%, 2v
2,6-(CH3)2, trace, 2w
Et3N
Pd(OAc)2
EtOH/H2O (2 mL/2 mL)
4 h, rt.
NC
NC
2-CH3, 65%, 2r
4-C2H5, 90%, 2s
10 h, rt
3-COCH3, 83%, 2g
3-CN 93%, 2h
step 1
one-pot step 2
3-NO2, 94%, 2i
O2N
O2N
3-OCH3, 73%, 2j
2-CN, 78%, 2k
Et3N for step 1
(equivalent)
Et3N for step 2
(equivalent)
Entry
Catalyst
Yield (%)
OCH3
2-OCH3, 92%, 2l
1
2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
Pd(OAc)2
－
0
24
47
84
82
81
0
－
－
2x, 92%
2y, 96%
OCH3
3
－
3
H3CO
3
－
3
OCH3
N
OCH3
4
3
OCH3
OCH3
5
5
3
2ab, 83%b
2z, 82%
6
5
6
2aa,80%
7
3
3
N
8
3
3
PdCl2
50
12
62b
OHC
N
9
3
3
Pd/C
2ac, traceb
2ad, traceb
HO
2ae, 96%c, 82%d
10
3
3
Pd(OAc)2
aReaction conditions: 4-hydroxybenzonitrile (0.5 mmol), SO2F2 balloon, base in
EtOH/H2O (2 mL/2 mL) at 25 C for 4 h, then phenylboronic acid (0.6 mmol), Pd
catalyst (1 mol%), base at 25 oC for 10 hours, isolated yield. bPd(OAc)2 (0.5 mol%).
HO
o
With the optimized reaction conditions in hand, the scope and
functional-group tolerance of phenols and arylboronic acids were
explored in this protocol. As shown in Table 2, in general, phenols
bearing both electron-withdrawing and electron-donating
substituted groups coupled with phenylboronic acid smoothly and
gave the biaryls product in good yields. Various functional groups,
including cyano, nitro, formyl, acetyl, methoxy, methyl, were all
tolerated to provide the corresponding products in high yields (Table
2, 2a-2f). In addition to the good functional-group compatibility,
meta-, ortho-substituted phenols were all tolerated in this system
(Table 2, 2g-2l). 2-Methoxyphenol with a steric effect could still
provide a 92% yield (Table 2, 2l). The reaction efficiency of this
process was further investigated by varying the arylboronic acids. To
our delight, arylboronic acids bearing electron-withdrawing groups,
which usually inactive for the Suzuki-Miyaura reactions, gave
excellent yields (Table 2, 2m-2o). For example, 4-
cyanophenylboronic acid and 4-fluorophenylboronic acid
successfully afforded the desired products in 94% and 90% yield,
respectively (Table 2, 2m and 2n). Arylboronic acid with groups at
F
OCH3
2af, no product
2ag, no product
N
N
O
O
2ah, 66%b
2ai, 52%b
aReaction conditions: Phenols (0.5 mmol), Et3N (1.5 mmol), SO2F2 gas balloon in
EtOH/H2O (2 mL/2 mL) at 25 oC for 4 h, then arylboronic acid (0.6 mmol), 1 mol%
Pd(OAc)2, Et3N (1.5 mmol) added to the mixture for 10 hours at 25 oC, isolated yield.
b80 oC for the second step. cpotassium 4-methylphenyltrifluoroboronate as
substrate. d4-methylphenylboronic acid pinacol ester.
in good yields (Table 2, 2q-2s). 4-Methoxyphenol underwent smooth
coupling with methyl substituted arylboronic acids (Table 2, 2t-2w).
Methoxy substituted boronic acids also carried out in this protocol
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and good product yields were observed (Table 2, 2x-2aa). An 82% transformations.19-23 Furthermore, these compounds were found to
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24, 25
DOI: 10.1039/D0OB00406E
yield was observed using quinolin-8-ol as substrate (Table 2, 2ab). be valuable for the design of targeted covalent drugs.
Therefore,
However, pyridin-4-ol and pyridin-2-ol were inactive under the same the screening of a library of chemically diverse fluorosulfates plays
conditions (Table 2, 2ac, 2ad). It was pleased to note that the an extremely important role in drug modification and discovery.
potassium
4-methylphenyltrifluoroboronate
and
4- Inspired by our previous work, we decided to synthesize bairy
methylphenylboronic acid pinacol ester were effective for this fluorosulfates by one-pot tandem reaction using 4-bromophenol as
process (Table 2, 2ae). In addition, ethynylestradiol as substrate was starting material. Two routes were proposed as shown in Table 3. For
examined. It was found that ethynylestradiol could covert to the route A, the Suzuki-Miyaura of 3a and arylboronic acids was
corresponding fluorosulfates smoothly at room temperature. carried out to produce 3b, then reacted with SO2F2 to obtain desired
Unfortunately, the cross-coupling product was not observed even biphenylsulfonyl fluoride. For the route B, 3a first reacted with SO2F2
o
increasing the second step temperature to 80 C (Table 2, 2af and to produce 3d, followed by cross-coupling with arylboronic acids to
2ag).
4-(Diphenylamino)phenol
coupled
with
(4- provide the biphenylsulfonyl fluoride product. Because both aryl
formylphenyl)boronic acid and (4-acetylphenyl)boronic acid to bromide and aryl fluorosulfate could couple with arylboronic acids,
provide the corresponding biaryls product in moderate yield (Table the key challenge is the chemselective cross-coupling of 3d. We were
2, 2ah and 2ai).
Fluorosulfates are readily available electrophiles and have been
reported for the building blocks in variety of synthetic
delighted to find the cross-coupling
a
Table 3 One-pot reaction for the synthesis of biphenylsulfonyl fluorides
O
S
B(OH)2
F
O
OH
R
OH
O
SO2F2
Route A
Pd(OAc)2
K2CO3
Et3N, 4.0 h, rt
R
Br
R
3b
not isolated
EtOH/H2O, rt
3a
3c
O
S
B(OH)2
F
O
R
OH
OSO2F
SO2F2
O
Route B
Et3N
EtOH/H2O, rt
Br
Pd(OAc), K2CO3, rt
Br
R
3d
3a
not isolated
3c
Key challage,
selective cross-coupling reaction
OSO2F
H3CO
OSO2F
OSO2F
3e, 89%a, 76%b
3f, 92%a, 74%b
3g, 85%a, 76%b
H3CO
H3CO
OSO2F
OSO2F
3h, 82%a, 75%b
OSO2F
3j, 78%a, 69%b
3i, 80%a, 74%b
F
OSO2F
OHC
OSO2F
Cl
OSO2F
3l, 72%a, 80%b
3m, 21%a, 71%b
OSO2F
3k, 74%a, 82%b
NC
OSO2F
OSO2F
3n, 32%a, 63%b
3o, 60%a, 45%b
3p, 78%a, 70%b
N
S
N
H3CO
OSO2F
3r, 58%a, 55%b
OSO2F
F
OSO2F
3q, 52%a, 49%b
3s, tracea, traceb
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Reaction conditions: aRoute A: 4-bromophenol (0.5 mmol), arylboronic acids (0.6 mmol), 1 mol% Pd(OAc)2, K2CO3 (1.0 mmol) in EtOH/H2O (2 mL/2 mL) at 25 oC for 2 h,
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then, Et3N (1.5 mmol) and SO2F2 gas were added to the mixture for 4h at room temperature, isolated yield. bRoute B: 4-bromophenol (0.5 mmol), Et3N (1.5 mmol) and
DOI: 10.1039/D0OB00406E
o
o
SO2F2 gas in EtOH/H2O (2 mL/2 mL) at 25 C for 4 h, then arylboronic acid (0.6 mmol), 1 mol% Pd(OAc)2, K2CO3 (1.5 mmol) added to the mixture for 2 hours at 25 C,
isolated yield.
Table 4 The preparation of terphenyls
B(OH)2
R1
OH
OSO2F
Route A
OH
SO2F2
Br
1 mol% Pd(OAc)2
2.0 equiv, K2CO3
EtOH/H2O, 2 h, rt
R1
R1
3.0 equiv Et3N
4.0 h, rt
4a
4b isolated
step 2
not isolated
step1
step 3
B(OH)2
R2
R2
R1
1 mol% Pd(OAc)2
EtOH/H2O
2.0 equiv, Et3N
80 oC, 12 h
4c
OCH3
OCH3
OCH3
CH3
OCH3
4e, 78% yield
4h, 83% yield
4d, 81% yield
4f, 70% yield
NC
H3CO
H3CO
4g, 42% yield
4i, 77% yield
OCH3
O
H3CO
H3CO
S
F
4j,43% yield
4k,36% yield
4l, 70% yield
Reaction conditions: step 1, bromophenol (0.5 mmol), arylboronic acids (0.6 mmol), K2CO3 (1.0mmol), EtOH/H2O (2 mL/2 mL), 25 ℃, 2 h, step 2: Et3N (1.5 mmol) and
SO2F2 by slowly bubbling from a balloon was added to the mixture for 4 h, 25 ℃. step 3: biphenylsulfonyl fluoride, arylboronic acid( 1.2 equiv), Pd(OAc)2(1 mol%), Et3N
(2.0 equiv), EtOH/H2O (2 mL/2 mL), under the air atmosphere, 80 ℃. Isolated yield.
reaction of bromides and boronic acids were more favorable by using further investigated and both routes provided the corresponding
inorganic bases K2CO3 at room temperature, which 3d was allowed products in moderate yields (Table 3, 3q-3s). However, almost no
to react with the boronic acid to afford the mono-substituted product was observed while using thiophen-2-ylboronic acid as
biphenylsulfonyl fluoride. To the best of our knowledge, this is the coupling partner.
first report to produce biarylsulfonyl fluoride by using one-pot
To further demonstrate the practicality of this cascade process,
protocol of sequential fluorosulfonation and Suzuki coupling. Next, we put our attention on the synthesis of terphenyls compounds
the scope and limitation for the both routes were explored. As shown which are important structural motif in various of liquid crystals and
in table 3, using 4-bromophenol as starting material, a wide range of fluorescent compounds and also exhibit various of significant
arylboronic acids bearing either an electron-donating group or an biological activities.26-32 As shown in table 4, the route A was applied
electron withdrawing group were examined. The results illustrate to produce biphenylsulfonyl fluoride due to the high activity. After
that the electronic nature of the substituent group on arylboronic isolated the biphenylsulfonyl fluoride product, the further cross-
acids has a significant influence on the reactivity. The route A coupling reaction of 4b and arylboronic acids was performed with 1
provided a higher product yields while using arylboronic acids mol% Pd(OAc)2 and 2.0 equiv. of Et3N at 80 oC in EtOH/H2O, and the
bearing electron-neutral and electron-rich groups (Table 3, 3e-3j). In overall yield was obtained after 12 hours. The scope and limitations
contrast, route B was more activity the while using arylboronic acids were examined and the results were showed in table 4. Methyl and
bearing withdrawing groups (Table 3, 3k-3n). 2-Methylphenylboronic methoxy ethyl substituted arylboronic acids were all successfully
acid afforded the desired product in moderate yields for the both transformed into their corresponding terphenyls in good yields
routes (Table 3, 3o). The scope of N-heteroaryl boronic acids were (Table 4, 4d-4f, 4h, 4i). But only a 42% yield was observed with (2-
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cyanophenyl)boronic acid (Table 4, 4g). Heteroaryl-substituted synthesis of biaryls. Particularly noteworthy with thisVpierwoAtortcicolelOisnliintes
ease in operation, but also its suitability for conversion of a broad
range of phenols into biphenylsulfonyl fluorides. Furthermore, a
series of p- and m-unsymmetrical terphenyls could be prepared in
good yields.
DOI: 10.1039/D0OB00406E
substrates on the 2-position produced their products 4k relatively
lower yields of 36% which could probably be attributed to the strong
electron-deficient property of the thiophene motif. m-Terphenyl was
aslo examined and a 70% yield was obtained (Table, 4l).
B(OH)2
CN
Experimental
CN
OH
CN
OSO2F
SO2F2,
2af
3.0 equiv Et3N, rt,
6 h, EtOH/H2O
General remarks
1 mol% Pd(OAc)2
not isolated
3.0 equiv Et3N, rt, 12 h
1.26 g, 81.5%
8 mmol
All commercially available reagents (from Acros, Aldrich, Fluka)
were used without further purification. The SO2F2 gas is
commercially available from Wuhan newradar special gas co.
LTD. NMR spectra were recorded on a Brucker Advance II 400
B(OH)2
OSO2F
OH
OSO2F
SO2F2
H3CO
3.0 equiv Et3N
Br
Br
1 mol% Pd(OAc),
3.0 equiv K2CO3,
6.0 h, rt
1
EtOH/H2O, 4.0 h, rt
3f
spectrometer using TMS as internal standard (400 MHz for H
H3CO
not isolated
8 mmol
NMR). All reactions were carried out under air atmosphere.The
isolated yields of products were obtained by short
chromatography on a silica gel (200-300 mesh) column using
petroleum ether (60-90 °C), unless otherwise noted.
1.81g, 80%
Scheme 1 Gram scale reactions
This one-pot protocol was performed for the preparation of
biarys and biphenylsulfonyl fluorides under gram-scale (Scheme 1).
As shown in Scheme 1, 2-cyano-4'-methylbiphenyl which is an
important unit in the drug of valsartan was observed by an 81% yield
with 1.26 g. 4'-Methoxy-[1,1'-biphenyl]-4-yl sulfofluoridate with an
80% yield was obtained at room temperature.
A plausible mechanism for SO2F2-mediated one-pot SM reaction
was proposed (Scheme 2). Initially, phenols reacted with SO2F2 gas
with the aid of Et3N and generated the aryl fluorosulfate
intermediate 1, which subsequently underwent an oxidative addition
with Pd0 to furnish Ar-Pd-OSO2F 2. Subsequently, a transmetallation
step where the trihydroxyboronate attaches to the palladium
intermediate generating Ar1-Pd(II)-Ar2 complex. Finally, the
reductive elimination of intermediate yielded the bairyl 4 while
regenerating the Pd0 .
General procedure for the coupling reaction of phenols and
arylboronic acids
A mixture of phenols (0.5 mmol), Et3N (1.5 mmol) was added to
a reaction flask (25 mL), before SO2F2 was introduced into the
mixture by slowly bubbling from a balloon, and the mixtures
was stirred in EtOH/H2O (2 mL/2 mL) at 25 oC for 4 hours. And
then arylboronic acid (0.6 mmol), 1 mol% Pd(OAc)2, Et3N (1.5
o
mmol) was added to the mixture for anthor 10 hours at 25 C.
Subsequently, the mixture was added to brine (10 mL) and
extracted with ethyl acetate (3 × 15 mL). The combined organic
layers were concentrated in vacuo and the product was isolated
by short chromatography.
General procedure for the preperation of biphenylsulfonyl
fluorides
Route A: A mixture of 4-bromophenol (0.5 mmol), arylboronic
acids (0.6 mmol), 1 mol% Pd(OAc)2, K2CO3 (1.0 mmol) EtOH/H2O
(2 mL/2 mL) were added to a reaction flask (25 mL), and the
mixture was allowed to stir at room temperature for 2 hours,
before a mixture of Et3N (1.5 mmol) and SO2F2 by slowly
bubbling from a balloon was added to the mixture for 4 hours
at room temperature. Subsequently, the mixture was added to
brine (10 mL) and extracted with ethyl acetate (3 × 15 mL). The
combined organic layers were concentrated in vacuo and the
product was isolated by short chromatography.
Route B: A mixture of 4-bromophenol (0.5 mmol), Et3N (1.5 mmol)
EtOH/H2O (2 mL/2 mL) was added to a reaction flask (25 mL), before
SO2F2 was introduced into the mixture by slowly bubbling from a
balloon, and the mixture was allowed to stir at room temperature
for 4 hours, then arylboronic acid (0.6 mmol), 1 mol% Pd(OAc)2,
K2CO3 (1.5 mmol) added to the mixture for 2 hours at room
temperature. Subsequently, the mixture was added to brine (10 mL)
and extracted with ethyl acetate (3 × 15 mL). The combined organic
Scheme 2 Plausible mechanism for one-pot SM reaction
Conclusion
In summary, we have developed
a mild one-pot sequential
fluorosulfonation and Suzuki–Miyaura reaction protocol for the
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layers were concentrated in vacuo and the product was isolated by
short chromatography.
10.
11.
12.
13.
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2275-2306.
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DOI: 10.1039/D0OB00406E
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H. Zeng, Z. Qiu, A. Domínguez-Huerta, Z. Hearne, Z.
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General procedure for the preperation of terphenyls
A mixture of bromophenol (0.5 mmol), arylboronic acids (0.6
mmol), 1 mol% Pd(OAc)2, K2CO3 (1.0 mmol) EtOH/H2O (2 mL/2
mL) were added to a reaction flask (25 mL), and the mixture was
allowed to stir at room temperature for 2 hours, before a
mixture of Et3N (1.5 mmol) and SO2F2 gas by slowly bubbling
from a balloon was added to the mixture for 4 hours at room
temperature. Then, the mixture was added to brine (10 mL) and
extracted with ethyl acetate (3 × 15 mL). The combined organic
layers were concentrated in vacuo and the product was isolated
by short chromatography. Subsequently, the product of
biphenylsulfonyl fluoride, arylboronic acid (1.2 equiv),
Pd(OAc)2(1 mol%), Et3N (2.0 equiv), EtOH/H2O (2 mL/2 mL), was
added to a reaction flask (25 mL), and the mixtures was stirred
in 80 oC for 12 hours. Then, the mixture was added to brine (10
mL) and extracted with ethyl acetate (3 × 15 mL). Finally the
combined organic layers were concentrated in vacuo and the
product was isolated by short chromatography.
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Acknowledgements
This work was financially supported by NSFC (Nos. 81660575
and 81360471), the United Scientific Research Foundation of
Zunyi Medical University (No. E-234), the Natural Science and
Technology Foundation of Guizhou Province [2018]1187.
C. Zhao, G.-F. Zha, W.-Y. Fang, K. P. Rakesh and H.-L.
Qin, Eur. J. Org. Chem., 2019, 2019, 1801-1807.
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Notes and references
†
Electronic supplementary information (ESI) available:
Characterization of cross-coupled products. See DOI:
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