Heteroannulation enabled by a bimetallic Rh(III)/Ag(i) relay catalysis: Application in the total synthesis of aristolactam BII

Article abstract of DOI:10.1039/c7cc02105d

A redox-neutral bimetallic Rh(iii)/Ag(i) relay catalysis allowed the efficient construction of 3-alkylidene isoindolinones and 3-alkylidene isobenzofuranones. The Rh(iii) catalyst was responsible for the C-H monofluoroalkenylation reaction, whereas the Ag(i) salt was an activator for the follow-up cyclization. The methodology developed was applied as a key step in the rapid total synthesis of the natural product aristolactam BII.

Full text of DOI:10.1039/c7cc02105d

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Heteroannulation Enabled by a Bimetallic Rh(III)/Ag(I) Relay
Catalysis: Application in Total Synthesis of Aristolactams BII
Received 00th January 20xx,
Accepted 00th January 20xx
Wei-Wei Ji, E Lin, Qingjiang Li and Honggen Wang*
DOI: 10.1039/x0xx00000x
www.rsc.org/
A redox-neutral bimetallic Rh(III)/Ag(I) relay catalysis allowed the
efficient construction of 3-alkylidene isoindolinones and 3-
alkylidene isobenzofuranones. The Rh(III) catalyst was responsible
for the C-H monofluoroalkenylation reaction, whereas the Ag(I)
salt was an activator for the follow-up cyclization. The
methodology developed was applied as a key step to the rapid
total synthesis of natural product aristolactam BII.
a) bio-active molecules containing 3-alkylidene isoindolinone and isobenzofuranone cores
O
O
OH
O
O
MeO
MeO
O
N
N
O
NH
O
O
OH
MeO
OH
OH
senkyunolide E
OH
MeO
Aristoyagonine
AKS 186
Aristolactams BII
Thunberginol F
b) reported synthesis of 3-alkylidene isoindolinones and isobenzofuranones via metal-catalysed C-H
annulation reaction
O
O
Isoindolinones and isobenzofuranones are important
heterocyclic compounds possessing diverse biological
properties. Among them, the 3-alkylidene isoindolinones and
Ar
R
O
N
OH
O
H
EWG
1
N
R
O
Ar
X
Pd, Co, Cu, Rh, Ru
Pd, Rh
O
(
X = COOH, H)
3
-alkylidene isobenzofuranones bearing an exocyclic double
1
2
(
2
R R CHCO) O
bond are of particular interest and have received considerable
Rh(III)-catalysed heteroannulation with 2,2-difluorovinyl tosylate
2
attention (Scheme 1a). Traditionally, the synthesis of these
c) previous work
detosylative cyclization
R
O
N
O
two heterocyclic scaffolds relied on reactions of heavily pre-
R
O
R = OMe
H+
3
N
functionalized substrates. Recently, with the development of
H
Rh(III)
R
N
F
H

organometallic chemistry, the transition-metal-catalysed C-H
annulation reaction provided a simple while flexible strategy
+
OTs
O
F
F
OTs
Ag(I)
R = Ts
N
R
O
4
F
1
2
for their synthesis from easily accessible starting materials.
&
d) this work
defluorinative cyclization
TsO
TsO
For examples, with benzamides or benzoic acids as substrates,
+
Rh(III)/Ag(I) relay catalysis + transformable OTs group
5
+ exclusive E-selectivity
+ easily accessible SM
&
application in total synthesis
the oxidative annulation reactions with activated alkenes,
6a,6c-e
6b,6f
e) Loh and Feng's work: Rh(III)-catalysed [4+1] annulation with gem-difluoroacrylate
terminal alkynes
or arylpropiolic acids
were known to
O
O
be effective for their construction (Scheme 1b). The use of
carboxylic anhydrides as coupling partner further broadened
Ts
F
Rh(III)
+
2
CO R
N
N Ts
H
F
the scope to the corresponding alkyl-substituted heterocycles
2
RO C
7
(
Scheme 1 b). Although elegant and useful, limitations such as
Scheme 1. Representative bio-active 3-alkylidene isoindolinones and 3-alkylidene
5c,6a-d,7
dependence
on
high
reaction
temperatures,
isobenzofuranones and their synthesis.
5
a,6a,6c,6e,6f
employment of stoichiometric amount of oxidants
7a
and/or unsatisfactory stereospecificities still remain. Of note,
the synthesis of heteroatom-substituted 3-alkylidene
isoindolinones or 3-alkylidene isobenzofuranones via C-H
activation strategy remains under-explored, although the
heteroatom substituent is expected to offer ample
opportunities for further decoration of the products.
Recently, our group reported the use of 2,2-difluorovinyl
1 in Rh(III)-catalysed C-H activation reactions for the
diverse synthesis of several types of fluorinated heterocycles.
With N-OMe benzamide as substrate, the coupling reaction
generated a monofluoroalkene intermediate
retention of the OTs functionality. By acidic hydrolysis of OTs,
we were able to realize the intramolecular cyclization to
furnish a six-membered fluorinated isoquinolin-1(2H)-one
product (Scheme 1c). We envisioned there might be an
tosylate
8
6a
2 with the
a.
School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006,
China, E-mail: wanghg3@mail.sysu.edu.cn
Electronic Supplementary Information (ESI) available: Detailed experimental
opportunity for 5-exo cyclization by taking advantage of the
9
procedures, characterization of starting materials and products and reactivity of monofluoroalkene. Specifically, the inductive
crystallographic data. See DOI: 10.1039/x0xx00000x
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effect of fluorine atom and its mesomeric p-π-interaction with loading of Ag(I) could be lowered to 20 mol %, with a good
View Article Online
DOI: 10.1039/C7CC02105D
alkene in
2 would render the α position susceptible to isolated yield of 83% being assured (entry 8). It should be
1
0
nucleophilic attack. In light of our continuing interest in noted only one stereoisomer was formed and the geometry of
combining C-H activation with catalyst relay for one-pot multi- the double bond was determined to be E based on X-ray
1
1
13
bonds forming reactions, we report herein our realization of crystallography analysis.
a bimetallic Rh(III)/Ag(I) based relay catalysis for the redox-
Table 2. Synthesis of 3-alkylidene isoindolinones.
neutral heteroannulation of benzamides or benzoic acids with
,2- difluorovinyl tosylate for the synthesis of OTs-
2
1
substituted 3-alkylidene isoindolinones and 3-alkylidene
isobenzofuranones, respectively (Scheme 1d). The Rh(III)
catalyst was responsible for the C-H monofluoroalkenylation
reaction, whereas the Ag(I) salt was an activator for the follow-
up cyclization. The manipulations of the OTs group allowed the
diverse synthesis of several isoindolinone derivatives. In
addition, the protocol developed was applied as a key step to
the synthesis of natural product aristolactams BII. During the
investigation of this project, Loh and Feng reported a Rh(III)-
catalysed [4+1] cyclization by using gem-difluoroacrylate as
a
6
AgOTf (20 mol %) was used instead of AgSbF .
1
2a
coupling partner.
With two-fold C-F bonds cleavage, the
The generality and limitation of the reaction were then
investigated. As shown in Table 2, a variety of differently
substituted N-tosylbenzamides were subjected. It was found
that the commonly encountered functional groups, regardless
of their electronic properities, including methyl (4b), methoxy
reaction allowed a redox-neutral construction of ester
substituted 5-methylene-1H-pyrrol-2(5H)-ones and isoindolin-
1
-ones (Scheme 1e).
a
Table 1. Reaction optimization.
(
4c), chloro (4l), bromide (4e
trifluoromethyl (4h 4k), ester (4j), cyanide (4i) and nitro (4o
were well tolerated. Methylthiol (4f) and dimethylamino (4p
, 4n), iodine (4d, 4m), phenyl (4g),
O
O
F
O
Ts
,
)
)
F
[Cp*Rh(CH CN) ][SbF ]
Ts
3
3
6
2
N
Ts
N
+
+
H
N
OTs
H
F
CsOPiv, additive
solvent , T, 16 h
OTs
TsO
groups, which would potentially poison both of the catalysts
also survived, although lower yields were obtained. The meta-
subsituted substrates delivered only one regioisomer, with the
reaction occurring at the less sterically hindered positions (4j-
3
a
1
4a
5
entry additive (x mol %) T (°C)
yield of 4a
n.d
yield of 5
86%
n.d
1
2
3
4
5
6
7
8
9
-
45
45
45
45
45
45
60
60
60
4p). Unfortunately, the ortho-substitutent (4q, 4r) residing in
AgOAc (50)
70%
n.d.
n.d.
75%
78%
90%
83%
77%
Cu(OTf)
AuCl(PPh
AgSbF
AgOTf (50)
AgSbF
AgSbF
2
(50)
34%
n.d.
n.d.
n.d.
n.d.
close proximity to the directing group retarded the reaction.
With the stereoselective synthesis of OTs-substituted 3-
alkylidene isoindolinones established, we set to explore the
analogous reaction by using benzoic acids as substrates. In this
case, the reaction of benzoic acid 6a with
of [Cp*Rh(CH CN) ](SbF ) directly provided the cyclization
3
) (50)
6
(50)
6
(50)
(20)
1 under the catalysis
6
n.d.
n.d.
3
3
6 2
13
AgOTf (20)
product 7a in 50% yield, together with 18% of six-membered
a
3
a (0.2 mmol), 1 (1.5 equiv), [Cp*Rh(CH
3
CN)
3
](SbF
)
6 2
(5 mol %), CsOPiv (1.0 heterocycle isochromen-1-one
8
(Table 3). With the addition of
was suppressed and an
equiv), additive (x mol %), CF CH OH (1.0 mL), T, 16 h, isolated yield.
3
2
AgSbF (10 mol %), the formation of
8
6
improved yield of 7a (78%) was obtained. The scope of this
reaction was also quite decent. Para- and meta-substituted
benzoic acids underwent smooth cyclization to give the
We initiated our study by reacting N-tosylbenzamide 3a with
1
under the catalysis of [Cp*Rh(CH CN) ](SbF ) (5 mol %).
3
3
6 2
o
With CsOPiv as base in CF CH OH at 45 C, the reaction
3
2
corresponding 3-alkylidene isobenzofuranones
7 in moderate
provided an open-chain monofluoroalkenylated product
5 in
to good yields. The survival of halide functional group (Br and I)
8
6% yield, with no cyclization product found (Table 1, entry 1).
Table 3. Synthesis of 3-alkylidene isobenzofuranones.
We envisioned the addition of π-acid to activate the
fluoroalkene might induce a one-pot cyclization. Indeed, the
use of AgOAc (50 mol %) as additive promoted the expected
defluorinative cyclization to give OTs-substituted 3-alkylidene
isoindolinones 4a in 70% yield (entry 2). Cu(OTf)2 and
O
O
[Cp*Rh(CH3CN)3](SbF6)2 (5 mol %)
O
Na2CO3 (1.0 equiv), HFIP (1.0 mL)
O
R
O
+
1
+
OH
R
AgSbF6 (10 mol %), 60 C, 16 h
OTs
without AgSbF6: 7a (50%), 8 (18%)
with AgSbF6: 7a (78%), 8 (trace)
TsO
7a
8
6a
AuCl(PPh ) were proven to be ineffective for the reaction
3
O
R
O
R = H, 7a 78%
R = Me, 7b 82%
R = OMe, 7c 75%
R = Ph, 7d 53%
7e
Me
O
(entries 3 and 4). Further screening demonstrated that AgSbF6
O
and AgOTf showed superior reactivity (entries 5 and 6). An
excellent yield of 90% was obtained when the reaction
temperature was increased to 60 °C (entry 7). Gratifyingly, the
O
R = Me, 7h 40%
R = OMe, 7i 57%
O
R
R = Br,
63%
TsO
TsO
R = I, 7f 49%
7g 60%
TsO
2
| J. Name., 2012, 00, 1-3
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provides additional handles for further decoration of the hemiaminal ether 12 was formed via the hydromethoxylation
View Article Online
DOI: 10.1039/C7CC02105D
7i) were also of the exocyclic double bond while stirring the methanol
products. Of note, ortho-substitutents (7h
,
tolerated to give acceptable yields.
solution of 4a in the presence of NaHCO . Full reduction of the
3
To gain mechanistic insight into the relay catalysis, control double bond and the OTs group was fulfilled by catalytic
experiments were conducted. Staring from monofluoroalkene hydrogenation with Pd/C. Finally, the N-tosyl group could be
1
5
5
, the reaction under the standard reaction conditions
provided the cyclization product 4a in 45% yield, confirming
that was an intermediate for the relay catalysis (eq 1). While
selectively removed upon the treatment with KPPh2.
5
O
O
PhB(OH)2, Pd2(dba)3
PCy3, K3PO4
NaHCO3
MeOH
the absence of Rh(III) catalyst provided a higher yield of 54%,
the omission of AgSbF gave no 4a at all, indicating Ag(I) was
the catalyst for the cyclization. In addition, the yield dropped
dramatically when CsOPiv was removed. Taking together,
these results concluded that both Ag(I) and base play crucial
role in the cyclization reaction.
N
Ts
Ts
N
Ts
Ts
dioxane 110 o
C
6
30 C, 12 h, 96%
9
O
12 h, 79%
TsO
Ph
12
O
O
O
PhSNa
CH3CN, RT
h, 72%
N
Ts
Pd/C, H2, MeOH
RT, 4 h, 79%
N
N
1
TsO
4
PhS 10
13
a
O
O
Zn, NH4OAc
EtOH
KPPh2
THF, -78
NH
N
Ts
C
2
h, RT, 60%
68%
14
11
TsO
Scheme 3. Derivatization of 4a.
A reaction mechanism was proposed to account for the
reaction outcome. Initially, Rh(III)-catalysed C-H activation which have been used as folk medicines in Eastern Asian.
Aristolactams belong to a large family of natural products
16
under the assistance of N-Ts group generates intermediate
Scheme 2). The coordination of is followed by a and B lymphocyte proliferation and exhibit cytotoxic activity.
regioselective olefin insertion to give III. A syn-coplanar
elimination provides the Z type monofluoroalkenylation several research groups. By using our methodology as key
I
Among them, aristolactam BII was found to be able to inhibit T
17
(
1

-F The total synthesis of aristolactam BII has been described by
18
8
product
5 with good stereoselectivity. We reasoned Ag(I) may reaction, this natural product was rapidly constructed (Scheme
act as a π acid to activate the olefin, thereby facilitating the 4). Thus, starting from benzamide 3s, the Rh(III)/Ag(I)-based
intramolecular cyclization reaction. Thus, the anti-addition to relay catalysis in HFIP produced 4s in 63% yield with excellent
the double bond resulted in a 5-exo cyclization to give
selective attack at the position of the F atom could be (2-hydroxyphenyl)boronic acid led to the successful
explained by the low-lying LUMO with large coefficient at this introduction of 2-hydroxylphenyl group to the scaffolds. After
V. The regio- and stereo-selectivity. The Suzuki-Miyaura coupling with
ɑ
1
0
position. Thereafter, an anti-coplanar
the stereospecific formation of

Z
-F elimination led to protected with trifluoromethylsulfonyl, compound 15 was
type 3-alkylidene converted to bromide 917 via OTf-bromo exchange under the
1
isoindolidone product 4a
.
catalysis of palladium. The treatment of 17 with AIBN and n-
Bu SnH, led to the debromocyclization and deprotection of the
3
18c
tosyl group, providing the target molecule aristolactam BII in
9
0% yield. It is worthy mention our synthetic route represents
2
0
the shortest one so far for the synthesis of aristolactam BII.
Scheme 2. Mechanistic proposal.
The synthetic utilities of the formed 3-alkylidene Scheme 4. Total synthesis of natural product aristolactam BII.
isoindolidones were evidenced by the facile transformation of
4
a
into a diverse array of isoindolidone derivatives (Scheme 3).
In conclusion, by taking advantage of the intriguing reactivity
For examples, the Suzuki-Miyaura coupling of the C-OTs bond of difluorovinyl tosylate, we have realized the efficient
14
with phenylboronic acid allowed the efficient synthesis of E- synthesis of 3-alkylidene isoindolinones and 3-alkylidene
isobenzofuranones via a Rh(III)/Ag(I) relay catalysis. The
methodology developed was applied to the rapid total
synthesis of aristolactam BII. Further explorations of gem-
difluoroalkene in relay catalysis are ongoing in our laboratory.
type phenylmethylene isoindolidone 9. The substitution of OTs
group with benzenethiolate was accomplished by reacting 4a
with sodium benzenethiolate in CH CN. Moreover, the OTs
3
group could be reduced with zinc in EtOH. Interestingly, a
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Zhu, P.-X. Li, J.-H. Zhang, J.-L. Niu and M.-P. Song, Org. Lett.,
Acknowledgement
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DOI: 10.1039/C7CC02105D
2
016, 18, 3610; (c) L.-B. Zhang, X.-Q. Hao, Z.-J. Liu, X.-X.
Financial support by the National Natural Science Foundation
of China (Nos. 21472250, 81402794 and 21502242), the Key
Project of Chinese National Programs for Fundamental
Research and Development (2016YFA0602900), and the
Zheng, S.-K. Zhang, J.-L. Niu and M.-P. Song, Angew. Chem.
Int. Ed., 2015, 54, 10012; (d) J. Zhang, H. Chen, C. Lin, Z. Liu, C.
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Gogoi, S. Guin, S. K. Rout, G. Majji and B. K. Patel, RSC Adv.,
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