Desulfinative palladium-catalyzed cross-coupling of arylsulfonyl hydrazides with aryl bromides under air

Article abstract of DOI:10.1002/aoc.5140

A highly efficient and mild palladium-catalyzed cross-coupling of arylsulfonyl hydrazides and aryl bromides for the selective synthesis of unsymmetrical biaryls has been developed. This methodology has the advantages of easily accessible starting materials, functional group tolerance and a wide range of substrates, which provide rapid access to biaryls derivatives. In this protocol, abundant and stable aryl bromides serve as the aryl sources by coupling reaction of the aryl group generated from arylsulfonyl hydrazides via in situ release of nitrogen and sulfur dioxide. No external oxidants or acids are needed for this kind of transformation.

Full text of DOI:10.1002/aoc.5140

Received: 18 January 2019
DOI: 10.1002/aoc.5140
Revised: 14 June 2019
Accepted: 3 July 2019
C O M M U N I C A T I O N
Desulfinative palladium‐catalyzed cross‐coupling of
arylsulfonyl hydrazides with aryl bromides under air
Qingling Liu | Bo Yang
Department of Chemistry and Chemical
A highly efficient and mild palladium‐catalyzed cross‐coupling of arylsulfonyl
Engineering, Xinxiang University,
Xinxiang 453003, People's Republic of
hydrazides and aryl bromides for the selective synthesis of unsymmetrical
China
biaryls has been developed. This methodology has the advantages of easily
Correspondence
accessible starting materials, functional group tolerance and a wide range of
substrates, which provide rapid access to biaryls derivatives. In this protocol,
abundant and stable aryl bromides serve as the aryl sources by coupling reac-
tion of the aryl group generated from arylsulfonyl hydrazides via in situ release
of nitrogen and sulfur dioxide. No external oxidants or acids are needed for this
kind of transformation.
Qingling Liu and Bo Yang, Department of
Chemistry and Chemical Engineering,
Xinxiang University, Xinxiang 453003.
People's Republic of China.
Email: xxliuqingling@163.com;
ytuyangbo@sina.com
KEYWORDS
aryl bromides, arylsulfonyl hydrazides, biaryls synthesis, Pd‐catalyzed cross‐coupling
[
19–23]
Stille[24–26] and
1
| INTRODUCTION
biphenyl derivatives are Suzuki,
Hiyama
[
27–29]
cross‐coupling reactions.
Biaryls are prominent structural motifs found in numer-
ous pharmaceuticals, bioactive molecules and natural
products. They exhibit a broad spectrum of biological
activities, and are employed extensively in various
Palladium‐catalyzed aryl–aryl coupling of aryl bro-
mides with arylboronic acid, organotin reagent, tri‐aryl
bismuth with arylhalides or triethoxy (aryl)silane have
been well‐established methods for the synthesis of
[1–3]
[30–33]
pharmaceutical and medicinal applications.
Transi-
biaryls.
However, previous reported methods have
tion metal‐catalyzed aryl−aryl bond‐forming reactions
some drawbacks, such as use of high catalyst loading, high
toxic organometallic reagents and low product yield. Thus,
the search for highly reactive coupling partners as substi-
tutes with aryl bromide has been a major concern.
Recently, aryl−aryl bond formation via C−S bond cleavage
has attracted considerable attention, and versatile
activated C−S bond‐containing partners, such as aryl
sulfonyl reagents, have been explored in cross‐coupling
reactions under transition metal catalysis. Commercial
represent powerful synthetic methods in organic
[4–8]
synthesis,
which have been broadly applied in
organometallic chemistry, materials science and medici-
[9–11]
nal chemistry.
Significant efforts have been devoted
to the development of transition metal‐catalyzed cross‐
coupling reactions, allowing for the construction of
[3,12–14]
novel and biologically relevant molecules.
Among
them, the palladium‐catalyzed coupling reactions for the
formation of carbon–carbon bonds have been widely
used both in preparative laboratories and industrial
[
5,34–36]
[37–42]
aryl sulfonyl halides,
zines
sulfinates
are recognized as the new aryl sources that
have been universally utilized in desulfinative arylation
and hydra-
[
42–51]
[15–18]
applications.
Catalysis using palladium as the tran-
[
52–54]
sition metal is certainly one of the most modern and
powerful strategies for aryl–aryl bond formation, and
the development of a new Pd‐catalyzed system has
aroused vigorous interest. The most frequently
employed methods for the synthesis of unsymmetrical
reactions recently (Scheme 1).
As we all known, arylsulfonyl hydrazides are relatively
stable, simple to handle and easy to prepare from their cor-
responding sulfonyl chlorides. Owing to these features,
they are regarded as particularly favorable aryl precursors
Appl Organometal Chem. 2019;e5140.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5140

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LIU AND YANG
[58]
[
57]
[49]
homocoupling,
iodination
and addition.
How-
ever, the new‐type Pd‐catalyzed desulfitative cross‐
coupling of arylsulfonyl hydrazides with aryl bromides
was still obscured. Herein, we would like to describe a sim-
ple and efficient palladium‐catalyzed cross‐coupling of
arylsulfonyl hydrazides and aryl bromides for the selective
synthesis of unsymmetrical biaryls. This transformation
proceeds under palladium/ligand‐catalyzed conditions,
providing excellent yields of coupling products and tolerat-
ing a variety of functional groups.
SCHEME 1 Biaryl synthesis with aryl bromide from different
coupling partners
2
| RESULTS AND DISCUSSION
To evaluate the feasibility of biaryl formation via a cat-
alytic desulfinative coupling of aryl bromide from sulfo-
nyl hydrazide precursors, we initiated our investigation
by studying a coupling reaction between phenylsulfonyl
hydrazide and phenyl bromide as a model reaction with
Cs CO in N,N‐dimethylacetamide (DMA) under an air
in desulfinative aryl–aryl cross‐coupling reactions by C−S
bond cleavage via release of SO and N . Zhong et al. first
employed arylsulfonyl hydrazides as aryl sources in
2
2
Suzuki‐type coupling reactions via desulfitation
[55]
processes.
Zhou's groups have employed arylsulfonyl
2
3
hydrazides as aryl sources in Hiyama coupling reactions
atmosphere. No cross‐coupling product was observed
when the reaction was carried out at 90°C using
[56]
by desulfitation.
Pd‐catalyzed desulfinative cross‐
coupling of arylsulfonyl hydrazides has been well studied,
5 mol% PdCl as the catalyst as determined by gas chro-
matography analysis. Under these conditions, several
2
[47]
[50]
such as Heck coupling,
Sonogashira coupling,
a,b
TABLE 1 Desulfinative coupling of phenylsulfonyl hydrazide with phenyl bromide with various ligands
a
Reaction conditions: phenylsulfonyl hydrazide (1.0 mmol), phenyl bromide (1.1 mmol), Pd (dppp)Cl
2 ml), 90°C, 6 hr.
2 2 3
(5 mol%), ligand (10 mol%), Cs CO (1.2 mmol), DMA
(
b
Isolated yields.

LIU AND YANG
3 of 7
other palladium salts were screened in the absence of
any ligand and proved to be ineffective for this
type of coupling reaction. Fortunately, the expected
product biphenyl was detected in 22% yield when Pd
TABLE 2 Desulfinative coupling of phenylsulfonyl hydrazides
with phenyl bromide with various catalysts, bases and solvents
a,b
(
dppp)Cl was used as the catalyst. Various ligands were
2
then screened in the presence of Pd (dppp)Cl (Table 1).
2
b
Entry
Catalyst
PdCl
Pd (OAc)2
Pd (acac)
Pd (PPh
Pd (dba)
Pd (CH CN)
Pd (PhCN)
Pd (dppf)Cl
Pd (PPh
Base
Cs CO
Cs CO
Solvent
Yield (%)
Nitrogen‐containing ligands such as phen (1,10‐
phenanthroline), DMAP (4‐dimethylaminopyridine) and
TEMDA (tetramethylethylenediamine) were ineffec-
tive, and their use resulted in lower yields (19–32%).
1
2
3
4
5
6
7
8
9
2
2
3
3
3
3
3
3
3
3
3
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
DMA
47
52
60
29
21
67
74
84
81
88
–
2
2
Cs
Cs
Cs
Cs
Cs
Cs
Cs
2
2
2
2
2
2
2
CO
CO
CO
CO
CO
CO
CO
The
introduction
of
dppf
[dichloro(1,1′‐bis
3 4
)
(diphenylphosphino)ferrocene)] gave modest yield.
2
While CM‐phos (2‐[2‐(dicyclohexylphosphino)phenyl]‐1‐
methyl‐1H‐indole) generated the desired products in
3
2 2
Cl
7
7% yield with phenylsulfonyl hydrazide and phenyl
bromide, the use of BINAP [bis (diphenylphosphino)‐
,1′‐binaphthalene)], Xantphos [4,5‐bis (diphenyl‐
phosphino)‐9,9‐dimethylxanthene] and DPEphos
bis[2‐(diphenylphosphino)phenyl] ether), resulted in a
2
Cl
2
2
1
3 3 2
) Cl
10
Pd (dppp)Cl
2
Cs
2
CO
3
(
11
–
Cs
2
CO
3
drop in the yield to 62%, 69% and 71%, respectively.
Interestingly, Xphos (2‐dicyclohexylphosphino‐2′,4′,6′‐
triisopropylbiphenyl) proved to be a better ligand for
the coupling reaction (85%). Among the phosphine
ligands investigated, Ruphos (2‐dicyclohexylphosphino‐
12
Pd (dppp)Cl
Pd (dppp)Cl
Pd (dppp)Cl
Pd (dppp)Cl
Pd (dppp)Cl
Pd (dppp)Cl
2
2
2
2
2
2
–
< 5
79
70
66
71
85
13
14
15
16
K
2
CO
Na CO
KOAc
3
2
3
2′,6′‐di‐i‐propoxy‐1,1′‐biphenyl) exhibited the best
NaOAc
CsF
reactivity, and biphenyl could be formed in 88% yield.
Encouraged by the aforementioned results, other reac-
tion conditions were investigated, including the choice of
catalysts, bases and solvents (Supporting information).
The results are summarized in Table 2. Among several cat-
17
a
Reaction conditions: phenylsulfonyl hydrazide (1.0 mmol), phenyl bromide
(1.1 mmol), catalyst (5 mol%), Ruphos (10 mol%), base (1.2 mmol), solvent
2 ml), 90°C, 6 hr.
(
b
Isolated yields.
alysts screened, Pd (acac) was found to be superior to var-
2
ious Pd (II) [PdCl and Pd (OAc) ] and Pd(0) [Pd (PPh )
3 4
2
2
and Pd (dba) ] salts (Table 2, entries 1–5). The introduction
Based on the optimized conditions, various aryl
2
of various palladium with nitrogen ligands [Pd
bromides with phenylsulfonyl hydrazide substituents
were screened to explore the scope and generality of
this reaction (Table 3, Supporting information). Various
electron‐donating and ‐withdrawing aryl bromides were
exposed to the reaction. Methoxyl substituents in para‐,
meta‐ and ortho‐positions yielded the corresponding
biaryls in similar yields ranging from 77% to 84%
(Table 3, 3a−3c). Weak electron‐donating units such as
p‐methyl, m‐methyl and m,m‐dimethyl were well toler-
ated to give the corresponding target compounds 3e–3g
ranging from 82% to 91%. Different halogens at the ben-
zene ring revealed only a small influence on the reactivity
(Table 3, 3h−3i). Application of the electron‐donating but
inductively electron‐withdrawing amine derivative deliv-
ered the corresponding product 3j in 66% yield, which
shows difficulties in several other biaryl syntheses. The
desired products could also be obtained in moderate yield
with chemical active aldehyde group (Table 3, 3k). The
electron‐poor phenyl bromides containing the electron‐
(
CH CN) Cl and Pd (PhCN) Cl ] did not increase the
3 2 2 2 2
yields (Table 2, entries 6 and 7). Among the Pd (II) catalysts
with phosphine ligands tested, Pd (dppp)Cl was the most
2
effective, affording the addition product in 88% yield [Pd
(
dppf)Cl , Pd (PPh ) Cl and Pd (dppp)Cl ; Table 2, entries
2 3 3 2 2
8–10]. In addition, no reaction was observed in the absence
of Pd catalyst (Table 2, entry 11), and only a trace amount
of the product was obtained when base was omitted from
the reaction (Table 2, entry 12). These results highlight
the importance of both the Pd catalyst and base for this
catalytic reaction. It was observed that most of the bases
(
K CO , Na CO , KOAc, NaOAc and CsF) could success-
2 3 2 3
fully promote the reaction (Table 2, entries 13–17). Among
these, Cs CO was determined optimum, and biphenyl
2
3
was isolated in 88% yield. After screening several combina-
tions of catalysts, bases and solvents, the reaction
proceeded in high yield when 5 mol% of Pd (dppp)Cl2
was employed in combination with Ruphos (10 mol%)
and Cs CO (1.2 equiv.) in DMA solvent at 90°C for 3 hr.
withdrawing NO group were converted to the desired
2
3
2

4
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LIU AND YANG
a,b
TABLE 3 Desulfinative coupling of phenyl sulfonyl hydrazides with various aryl bromides
a
Reaction conditions: phenylsulfonyl hydrazide (1.0 mmol), aryl bromide (1.1 mmol), Pd (dppp)Cl
2 ml), 90°C, 6 hr.
2
(5 mol%), Ruphos (10 mol%), Cs
2
CO
3
(1.2 mmol), DMA
(
b
Isolated yields.
product 3l−3m in 74–78% yields (Table 3, 3l−3m).
Finally, aryl bromides with extended π‐systems were
employed affording terphenyl derivative 3m in 85% yield
and naphthalene derivative 3o in 71% yield, respectively.
To our delight, heteroaryl bromides such as thiazolyl bro-
mide 3p achieved a satisfactory conversion in 75% yield.
The scope of aromatic sulfonyl hydrazides with
para‐methoxyphenyl bromide was next examined
(Table 4, Supporting information). The para‐substituted
phenyl sulfonyl hydrazides bearing both electron‐donating
and electron‐withdrawing groups regioselectively afforded
the coupled products in moderate to good yields (Table 4,
a,b
TABLE 4 Desulfinative coupling of various arylsulfonyl hydrazides with phenyl bromide
a
2 2 3
Reaction conditions: arylsulfonyl hydrazide (1.0 mmol), para‐methoxy‐phenyl bromide (1.1 mmol), Pd (dppp)Cl (5 mol%), Ruphos (10 mol%), Cs CO
(
1.2 mmol), DMA (2 ml), 90°C, 6 hr.
b
Isolated yields.

LIU AND YANG
5 of 7
4
a−4f). When a meta‐substituted phenylsulfonyl hydra-
styrylsulfonyl hydrazide with bromobenzene (Scheme 2,
E and F).
zide was used, the desulfinative coupling occurred, provid-
ing the meta‐arylation product (Table 4, 4g). The coupling
of 2,5‐dimethyl and 2,5‐difluoro phenylsulfonyl
hydrazides with para‐methoxyphenyl bromide gave the
A putative reaction mechanism was then proposed in
[
51,59]
Scheme 3.
In the first stage, oxidative addition of aryl
bromide with Pd (0) into the C‐Br bond formed intermedi-
ate A. Subsequently, ligand exchange of the arylsulfonyl
hydrazide with intermediate A further eliminated a
molecule of HBr to convert to arylpalladium hydrazine
intermediate B with the assistance of base. (Arylsulfonyl)
2
,5‐disubstituted biaryls in good yields (Table 4, 4h−4i).
In addition, para‐amino phenylsulfonyl hydrazide was
amenable to afford the desired product in 69% yield
(
(
Table 4, 4j). To our delight, the chloro substitutents
Table 4, 4k) can be tolerated under standard conditions,
which would be beneficial for further modification of these
products considering the various transformations based on
aryl halides. Heteroaryl sulfonyl hydrazides, such as 2‐
pyridinyl substituted sulfonyl hydrazides, afforded the cor-
responding product in 71% yield (Table 4, 4l).
To gain insights into the reaction mechanism, a control
experiment between phenylsulfonyl hydrazide and phenyl
bromide in the presence of 2 equiv. of TEMPO or BHT was
performedunder otherwise identical conditions (Scheme2,
A and B). These results excluded the possibility of radical
formation through desulfination. Notably, gram‐scale
synthesis of biaryl was achieved successfully, demonstrat-
ing the synthetic practicality of the reaction (Scheme 2,
C). Unfortunately, when alkyl sulfonyl hydrazide or alkyl
bromide was applied, no desired product could be isolated
in the complicated reaction mixture (Scheme 2, D).
Interestingly, 1‐bromocyclohexene could react with
phenylsulfonyl hydrazide under standard conditions, and
5
1% yield of styrene was obtained by the coupling of
SCHEME 3 Proposed mechanism of desulfinative coupling
SCHEME 2 Control experiments of the
desulfinative coupling

6
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LIU AND YANG
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In summary, we have developed an efficient protocol for
the preparation of various biaryl derivatives by using aryl
bromides that are cheap and available, and arylsulfonyl
hydrazides as the aryl source under mild conditions.
Different substituted arylsulfonyl hydrazides and various
simple aryl bromides could be tolerated, affording biaryls
in moderate to good yields. This method allowed easy
access to significant functional biaryls for potential appli-
cations in medicinal and organic chemistry.
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ORCID
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Bo Yang https://orcid.org/0000-0002-8092-7708
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How to cite this article: Liu Q, Yang B.
Desulfinative palladium‐catalyzed cross‐coupling of
arylsulfonyl hydrazides with aryl bromides under
air. Appl Organometal Chem. 2019;e5140. https://
doi.org/10.1002/aoc.5140
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