Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates

Article abstract of DOI:10.1002/ejoc.202000176

The first general palladium-catalyzed α-arylation of arylacetonitriles with aryl and heteroaryl sulfonates are reported. Pd(OAc)₂ associated with XPhos serves as the effective catalyst to facilitate this reaction. A broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl/heteroaryl tosylates and mesylates are coupled with arylacetonitriles bearing different substituents to give the corresponding products in good to excellent yields. Catalyst loading down to 0.1 mol-% Pd was achieved, and 22 unprecedented compounds were synthesized from 43 demonstrated examples using this method. Its applicability with the modification of biological phenolic compounds was successfully demonstrated. The Pd/XPhos system catalyzed the α-arylation and followed by alkylation in one-pot sequential conditions, resulting in the direct synthesis of compounds containing quaternary center- and deuterium-containing compounds in good to excellent yields.

Full text of DOI:10.1002/ejoc.202000176

A Journal of
Accepted Article
Title: Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with
Aryl Tosylates and Mesylates
Authors: On Ying Yuen, Xiangmeng Chen, Junyu Wu, and Chau-Ming
So
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10.1002/ejoc.202000176
European Journal of Organic Chemistry
COMMUNICATION
Palladium-Catalyzed Direct -Arylation of Arylacetonitriles with
Aryl Tosylates and Mesylates
On Ying Yuen,[a] Xiangmeng Chen,[a] Junyu Wu,[a] and Chau Ming So*[a,b]
Dedication ((optional))
[a]
[b]
Dr. On Ying Yuen, Mr. Xiangmeng Chen, Mr. Junyu Wu, and Dr. Chau Ming So
State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology
The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong
E-mail: chau.ming.so@polyu.edu.hk
URL: http://www.cmsolab.com
Dr. Chau Ming So
The Hong Kong Polytechnic University, Shenzhen Research Institute
Shenzhen, People’s Republic of China
Supporting information for this article is given via a link at the end of the document.((Please delete this text if not appropriate))
Abstract: The first general palladium-catalyzed -arylation of
arylacetonitriles with aryl and heteroaryl sulfonates are reported.
Pd(OAc)2 associated with XPhos serves as the effective catalyst to
facilitate this reaction. A broad range of electron-rich, -neutral, -
deficient, and sterically hindered aryl/heteroaryl tosylates and
mesylates are coupled with arylacetonitriles bearing different
substituents to give the corresponding products in good to excellent
yields. Catalyst loading down to 0.1 mol% Pd was achieved, and 22
unprecedented compounds were synthesized from 43 demonstrated
examples using this method. Its applicability with the modification of
biological phenolic compounds was successfully demonstrated. The
Pd/XPhos system catalyzed the -arylation and followed by alkylation
in one-pot sequential conditions, resulting in the direct synthesis of
compounds containing quaternary center- and deuterium-containing
compounds in good to excellent yields.
preparation and unique substitution pattern. Phenolic moieties are
also commonly presented in biologically active compounds.[13]
The usage of these phenolic moieties enables the rapid
modification and derivatization which greatly facilitate the
structure refinement and structure-activity relationship study.
However, the reaction conditions such as strong base and high
temperature employed in palladium-catalyzed direct arylation
reactions with aryl halides are too harsh for frequently used
phenolic derivatives. A strong base, such as NaHMDS[10a] or KOt-
Bu,[10b] is generally required for the direct deprotonation of the
benzylic CH2 proton. To the best of our knowledge, the general
palladium-catalyzed -arylation of arylacetonitriles with aryl
sulfonates even for most common aryl triflates has not been
reported.
Diarylacetonitriles are important motifs in many natural products
and pharmaceutically active molecules (Figure 1).[1] The nitrile
moiety is a versatile functional group that allows further organic
transformations that afford corresponding substituted benzoic
acids/esters, amides, amines, aldehydes, and nitrogen-containing
heterocycles[ 2 ] and offer the diarylmethane unit for natural
products synthesis[3]. Traditional methods for preparing -aryl
nitriles include the Friedel-Crafts reactions,[4] dehydration of -
substituted amides,[5] cyanation of benzyl alcohols and halides,[6]
and decarboxylative arylation of potassium cyanoacetate.[ 7 ]
Among these methods, palladium-catalyzed -arylation of nitriles
with aryl halides is an efficient method to synthesize -aryl
nitriles,[8] which was independently developed by the Hartwig,[9]
Verkade[10] and other[11] research groups. Nambo reported the
selective synthesis of multi-arylated acetonitriles via sequential
palladium-catalyzed arylations of chloroacetonitrile.[12]
Despite the fact that aryl halides are prevalent electrophiles in
-arylation of nitriles because of their ease of oxidative addition
and non-sensitive towards strong basic condition, halogenated
compounds are not common in view of medicinal chemistry.
Lengthy synthetic pathways and functional group manipulations
are required to perform the halogenation of specific sites in natural
products or pharmaceuticals. Aryl electrophiles generated from
phenolic compounds are highly desirable because of their easy
Figure 1. Examples of useful intermediates and products containing
diarylacetonitriles motifs.
We envisioned that using relatively stable, easily accessible,
and inexpensive aryl mesylates and tosylates could be used as
the attractive electrophiles for the arylation reaction.[14] However,
several challenging issues associated with the reaction have to
be resolved: (1) phenolic derivatives and cyano group suffer from
severe hydrolysis under the strong alkaline reaction conditions;
(2) base-sensitive functional groups are not compatible; (3)
further arylation may occur due to the increased acidity of the
remaining -C-H bonds after the first step of arylation of
arylacetonitriles, resulting in undesirable mixtures; (4) the
competitive coordination of the cyano group may retard the
desired reaction; (5) the oxidative addition of relatively inert aryl
mesylates and tosylates required electron-rich phosphine, yet it
may significantly increase the difficulty of completing reductive
1
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10.1002/ejoc.202000176
European Journal of Organic Chemistry
COMMUNICATION
elimination step in the -arylation reaction.[15] Given our research
group’s persistent interest in palladium-catalyzed direct C-H
arylation with challenging electrophiles,[15c, 16] we herein report our
effort in the first general palladium-catalyzed -arylation of
arylacetonitriles with aryl tosylates and mesylates (Scheme 1).
yields (78-99%). CataCXium®A and dppf were found to be
ineffective. CM-Phos, SPhos, XPhos, and BrettPhos gave
comparable product yields. When catalyst loading was reduced to
0.1 mol% Pd, XPhos provided the best product yield (82%).
After identifying the best ligand, we turned our attention to
optimizing the reaction conditions (Table 2). Commonly used
solvents were screened (Table 2, entries 1-8), and t-BuOH was
found to be the best solvent in this reaction. Several inorganic
bases were also surveyed. Notably, mild bases (e.g., K3PO4 and
K2CO3 vs. LiOt-Bu) were able to promote this reaction, which
reduced the undesirable reactions such as the formation of multi-
arylated mixtures and hydrolyzed side products from nitriles and
aryl sulfonates (Table 2, entry 17 vs. entry 18). An organic base
(Et3N) afforded poor product yield (Table 2, entry 16). Pd(OAc)2
exhibited the best performance among the palladium sources
examined (Table 2, entries 18-21).
Table 2. Optimization of reaction conditions for palladium-catalyzed -arylation
of benzyl cyanide with 2-naphthyl tosylate[a]
Entry
Pd (mol% Pd)
solvent
base
%yield[b]
Scheme 1. Palladium-catalyzed -arylation of arylacetonitriles.
Table 1. Evaluation of Ligand Efficacy[a]
1
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (1)
Pd(OAc)2 (0.1)
Pd(OAc)2 (0.1)
Pd(TFA)2 (0.1)
Pd(ACN)2 (0.1)
Pd2(dba)3 (0.1)
t-BuOH
MeOH
LiOt-Bu
LiOt-Bu
LiOt-Bu
LiOt-Bu
LiOt-Bu
LiOt-Bu
LiOt-Bu
LiOt-Bu
K3PO4
K2CO3
Cs2CO3
Na3PO4
NaOAc
KOAc
92
4
2
3
CPME
75
59
20
64
42
0
4
Dioxane
THF
5
6
Toluene
DMF
7
8
CH3CN
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
t-BuOH
9
93
87
0
10
11
12
13
14
15
16
17
18
19
20
21
71
2
0
KF
30
15
82
89
35
82
65
[a] Reaction conditions: 2-naphthyl tosylate (0.5 mmol), benzyl cyanide (0.6
mmol), Pd(OAc)2, (2 mol%), L (8 mol%), LiOt-Bu (1.0 mmol) and t-BuOH (1.5
ml) were stirred at 110 oC under N2 for 4 h. Calibrated GC yields were reported
using dodecane as the internal standard. [b] 0.5 mol% Pd. [c] 0.1 mol% Pd were
used.
Et3N
LiOt-Bu
K3PO4
K3PO4
K3PO4
K3PO4
During the initial investigation, 2-naphthyl tosylate (1a) and
benzyl cyanide (2a) were chosen as the benchmark substrates. A
number of previously reported remarkable ancillary ligands were
examined for their potential effectiveness in this -arylation
process (Table 1). Preliminary screening employed indolyl (CM-
Phos), benzimidazoly (PhMezole-Phos), Buchwald’s biaryl
(SPhos, XPhos, and BrettPhos), and Stradiotto’s P,N-type
phosphine ligands (MorDalPhos), resulting in good product
[a] Reaction conditions: 2-naphthyl tosylate (0.5 mmol), benzyl cyanide (0.6
mmol), Pd(OAc)2/XPhos = 1:4 (mol % as indicated), base (1.0 mmol), solvent
2
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10.1002/ejoc.202000176
European Journal of Organic Chemistry
COMMUNICATION
(1.5 ml) were stirred at 110 oC under N2 for 4 h. Calibrated GC yields were
reported using dodecane as the internal standard.
excellent product yields (Table 3, compounds 3pa and 3qa). In
addition, our protocol allowed for modification of the human sex
hormone 17-estradiol. Tosylated and mesylated 17-estradiol
were smoothly coupled with benzyl cyanide to produce the
corresponding products (Table 3, compounds 3ra and 3sa).
Table 3. Palladium-catalyzed -arylation of benzyl cyanide with aryl tosylates
and mesylates[a]
Table 4. Palladium-catalyzed -arylation of arylacetonitriles with aryl tosylates
and mesylates[a]
[a] Reaction conditions: ArOTs or ArOMs (0.5 mmol), benzyl nitrile derivatives
(0.6 mmol), Pd(OAc)2/XPhos = 1:4 (mol % as indicated), K3PO4 (1.0 mmol) and
t-BuOH (1.5 ml) were stirred at 110 oC under N2 for 4 h. Isolated yields were
reported. [b] K2CO3 was used instead of K3PO4.
To further expand the substrate scope, we next investigated
whether other arylacetonitriles could act as the cross-coupling
partners (Table 4). 4-Me, 4-Ph, 3-OMe substituted
arylacetonitriles were found to be applicable substrates (Table 4,
compounds 3ab, 3ob, 3ac, 3ac, 3bc, 3cd, 3ad, 3ee, and 3oe).
Electron-poor arylacetonitriles were suitable counterparts and
afforded the corresponding products in good to excellent yields
(76-93% yield) (Table 4, compounds 3kf, 3cf, and 3ag). Our
system was also capable of handling sterically hindered
arylacetonitriles and exhibited good reactivity (Table 4,
compounds 3ah and 3fh). Arylacetonitriles containing C(O)OMe
group was also found to be compatible under these mild reaction
conditions (Table 4, compounds 3ai and 3oi).
[a] Reaction conditions: ArOTs or ArOMs (0.5 mmol), benzyl cyanide (0.6
mmol), Pd(OAc)2/XPhos = 1:4 (mol % as indicated), K3PO4 (1.0 mmol) and t-
BuOH (1.5 ml) were stirred at 110 oC under N2 for 4 h. Isolated yields were
reported. [b] K2CO3 was used instead of K3PO4.
Once the optimized reaction conditions were established, the
efficacy of the catalyst system in -arylation of benzyl cyanide
was then evaluated with a wide range of aryl tosylates and
mesylates (Table 3). In general, 0.5-2.0 mol% Pd completed the
cross-couplings of benzyl cyanide. Electron-neutral and -rich
arenes were converted to the corresponding products in good to
excellent product yields (Table 3, compounds 3aa-3ha). Electron-
deficient arenes, which proved to be difficult substrates in a-
arylation, gave good product yields (Table 3, compounds 3ia and
3ja). Sterically hindered substrates were also found to be
applicable in our system (Table 3, compounds 3ka-3ma).
Common functional groups such as ketone and ester were
compatible under these mild basic reaction conditions (Table 3,
compounds 3na and 3oa), and heteroaryl tosylates and
mesylates were also used as the coupling partners to give
Apart from aryl sulfonates, alkyl and allylic tosylates can also
be employed as electrophiles for the further construction of
quaternary center-containing compounds which can be accessed
via a simple one-pot, two-step approach. The two-step reactions
were successfully achieved by adding the second electrophilic
partner (alkyl or allylic tosylates) after the first step of -arylation
3
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10.1002/ejoc.202000176
European Journal of Organic Chemistry
COMMUNICATION
reaction in one-pot (Table 5). Moreover, accessing deuterium
compounds in good yields using the deuterated alkyl tosylates is
remarkable because it can be easily synthesized using relatively
inexpensive deuterated alcohol (Scheme 2). It is particularly
noteworthy that no reaction work-up was performed and no
additional catalyst was added prior to the second step in the
reaction sequence.
Acknowledgements
We thank the Shenzhen Strategic New Industry Development
Research Fund of Shenzhen Science, Technology and Innovation
Commission (SZSTI) (JCYJ20180306173843318), National
Natural Science Foundation of China (21972122) and the
Research Grants Council of Hong Kong, Early Career Scheme
(ECS
25301819) for financial support. We are grateful to Mr.
Table 5. Synthesis of quaternary center-containing compounds through one-pot,
two-step palladium-catalyzed -arylation of arylacetonitriles with aryl tosylates
and alkyl tosylates[a]
Hang Wai Pang for his assistance in preparing some aryl
sulfonates, Ms. Ka Mon Yu and Ms. Shan Shan Ng for their
assistance in supplementary material preparation, and Dr. Pui Kin
So (University research facilities in Life Science, PolyU) for HRMS
analysis.
Keywords: Palladium • Phosphine ligands • -Arylation• Aryl
sulfonates • Nitriles
[1]
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[a] 1st-step reaction conditions: ArOTs (0.5 mmol), benzyl nitrile derivatives (0.55
mmol), Pd(OAc)2 (2 mol%), XPhos (8 mol%), K3PO4 (1.0 mmol) and t-BuOH(1.5
ml) were stirred at 110 oC under N2 for 4 h. 2nd-step reaction conditions: R’’-OTs
(0.75 mmol) and K3PO4 (1.0 mmol) were stirred at 110 oC under N2 for 4 h.
Isolated yields were reported. [b] 7 h was conducted in 2nd-step.
[2]
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In conclusion, we report the first general palladium-catalyzed
direct -arylation of arylacetonitriles using aryl/heteroaryl
tosylates and mesylate as the electrophilic coupling partners.
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catalytic
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exhibited
excellent
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compatibility with a wide range of functional groups. Furthermore,
this method provided a straightforward modification of biologically
active phenolic compounds. The catalyst loading could be
achieved with as low as 0.5 mol% of palladium catalyst. -
arylation and -alkylation in a one-pot sequential manner for the
direct synthesis of quaternary center- and deuterium-containing
compounds were achieved in good to excellent yields. This
general catalyst system offers a convenient synthetic pathway to
access versatile diaryl acetonitriles via abundant phenolic
compounds.
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Scheme 2. Synthesis of deuterium compounds[a] ([a] 1st-step reaction
conditions: ArOTs (0.5 mmol), benzyl nitrile derivatives (0.55 mmol), Pd(OAc)2,
(2 mol%), XPhos (8 mol%), K3PO4 (1.0 mmol) and t-BuOH (1.5 ml) were stirred
at 110 oC under N2 for 4 h. 2nd-step reaction conditions: CD3OTs (0.75 mmol)
and K3PO4 (1.0 mmol) were stirred at 110 oC under N2 for 4 h. Isolated yields
were reported. [b] 7 h was conducted in 2nd-step.
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4
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European Journal of Organic Chemistry
COMMUNICATION
[14] According to 2019 Aldrich catalog: mesyl chloride (USD158.01/L), tosyl
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5
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COMMUNICATION
-Arylation
The first general palladium-catalyzed -arylation of arylacetonitriles with aryl and heteroaryl sulfonates are reported. The catalyst
system comprising of Pd(OAc)2 and XPhos is highly effective towards this reaction. A wide range of aryl/heteroaryl tosylates and
mesylates are coupled with arylacetonitriles smoothly and catalyst loadings as low as 0.1 mol% Pd can be achieved.
Institute and/or researcher Twitter usernames: bccmso
6
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