Photocatalytic acylarylation of unactivated alkenes with diaryliodonium salts toward indanones and related compounds

Article abstract of DOI:10.1039/c8cc02636j

A novel photocatalytic acylarylation of unactivated alkenes using diaryliodonium salts as the arylation reagent is described. The reaction produces a variety of 2-benzyl indanones, 3,4-dihydronaphthalen-1(2H)-ones, and 2,3-dihydroquinolin-4(1H)-ones in pr

Full text of DOI:10.1039/c8cc02636j

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Photocatalytic acylarylation of unactivated alkenes with
diaryliodonium salts toward indanones and related compounds
Yongtao Chen, Chenyun Shu, Fang Luo, Xiaohui Xiao,∗ and Gangguo Zhu∗
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
A novel photocatalytic acylarylation of unactivated alkenes using alkenes and a subsequent dehydrogenative addition to aldehydes
diaryliodonium salts as the arylation reagent is described. The might offer an alternative pathway for the alkene acylarylation. On
reaction produces
a variety of 2-benzyl indanones, 3,4- the other hand, diaryliodonium salts are widely used as the aryl
dihydronaphthalen-1(2H)-ones, and 2,3-dihydroquinolin-4(1H)- radical source in organic synthesis.12,13 Particularly, enabled by the
ones in promising yields with excellent diastereoselectivity under rapid development of photoredox catalysis,14 the alkene
very mild conditions, which may be appealing for the synthesis of arylfunctionalization, such as oxyarylation,13a-c aminoarylation,13a
biologically active molecules.
and desulfonylative arylation,13d has been realized with
diaryliodonium salts under very mild reaction conditions. Inspired
by these promising results, we present here a novel photocatalytic
acylarylation of simple alkenes using readily accessible
diaryliodonium hexafluorophosphates as the arylation reagent,
Difunctionalization of alkenes has emerged as a very powerful tool
for the rapid assembly of important building blocks of natural
products and pharmaceutical compounds because of its high
reaction efficiency and molecule diversity.1 In particular, the radical
acylarylation of alkenes attracts more and more attention in the
past few years.2-9 For example, Li and co-workers reported a TBHP-
promoted dehydrogenative coupling of aldehydes with N-
arylacrylamides, giving a direct access to 3-(2-oxoethyl)indolin-2-
ones in moderate to high yields (Scheme 1a).2 Later, a variety of
alkene acylarylation has developed by using α-oxocarboxylic acids,4
carboxylic acids,5 benzoins,6 aromatic carboxylic anhydrides,7 or α-
diketones8 as the acylation reagent. It should be noted that the
previous methods are mainly restricted to the utilization of
activated alkenes, while the more common, unactivated alkenes
still remain challenging partners for this transformation.9 Moreover,
the traditional methods2-8 involve the addition of acyl radicals to
alkenes, followed by a subsequent intramolecular arylation. In
contrast, the reaction triggered by radical arylation of alkenes has
not been achieved yet. Therefore, the exploration of a novel, mild,
and general protocol that enables the acylarylation of simple
alkenes is highly demanded.10
which produces
a
series of cyclic ketones such as 2-benzyl
and 2,3-
indanones, 3,4-dihydronaphthalen-1(2H)-ones,
dihydroquinolin-4(1H)-ones at room temperature (Scheme 1b).
Notably, trans-2,3-disubstituted indanones can be exclusively
assembled via this method. The mild reaction conditions, high
efficiency, broad substrate scope, and excellent diastereoselectivity
render it an attractive method for the fast construction of
biologically active molecules like indanones. As compared to the
traditional methods depending on sequential acylation/arylation,
this reaction proceeds via the tandem radical arylation/acylation
pathway, thus offering a new possibility for the acylarylation of
alkenes, especially the unactivated ones.
(a) traditional methods: tandem acylation/arylation of activated alkenes2-8
R4
O
R3
R3
O
conditions
R1
+
R1
O
R4
Y = H, CO2H, COR, OCOAr, CH(OH)Ph
Y
N
N
R2
O
R2
Recently, we started a project on the development of catalytic
radical transformation of aldehydes.11 As an example, an oxidative
radical addition strategy has been developed for the rapid synthesis
of ketones featuring the attack of carbon radicals to aldehydes.11
Following this concept, we reasoned that the radical arylation of
(b) this work: tandem arylation/acylation of unactivated alkenes
O
O
Ar
Ir(ppy)2(dtbbpy)PF6
white LED, DMSO, rt
H
R1
R1
+ Ar2IPF6
n
R2
n = 5 or 6
R2
first tandem radical arylation/acylation of unactivated alkenes
excellent diastereoselectivity (dr > 98:2)
mild conditions and broad substrate scope
a Key Laboratory of the Ministry of Education for Advanced Catalysis Materials,
Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua
321004, P. R. China. E-mail: xxh@zjnu.cn, gangguo@zjnu.cn
Scheme 1 Summary of radical acylarylation of alkenes.
Electronic Supplementary Information (ESI) available: Experimental details and
spectra of all new products. See DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
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disubstituted indanones 3k-3m in good yields, which were
determined by the NOE measurements. Furthermore, the
substitution of the C-C double bond of 1 with substituents like
methyl group led to a decline in the yield (3o and 3p), presumably
due to the increased steric hindrance of alkene. In addition to the
generation of indanone derivatives, this reaction can be applicable
for the construction of other cyclic ketones. For instance, the
coupling of 1q with 2a occurred efficiently to deliver the 3,4-
dihydronaphthalen-1(2H)-one 3q in 66% yield. Facile conversion of
1s into the 2,3-dihydroquinolin-4(1H)-one derivative 3s was also
feasible. In contrast, substrates 1t and 1u, possessing an activated
alkene, were not engaged in this reaction (3t and 3u).
At the outset, we screened the photoredox catalyst by examining
the reaction between 2-allyl benzaldehyde (1a) and
diphenyliodonium hexafluorophosphate (2a) in DMSO using a 8 W
o
white LED at room temperature (25 C). When 2 mol% of
Ru(bpy)3Cl2 was employed as the catalyst, the 2-benzyl indanone 3a
was obtained in 16% yield (Table 1, entry 1). To our delight, the
yield was increased to 70% by switching the photoredox catalyst
from Ru(bpy)3Cl2 to Ir(ppy)2(dtbbpy)PF6 (entries 2-4). Meanwhile,
we tested other diphenyliodonium salts including the
tetrafluoroborate (2b) and triflate (2c); however, reduced yields
were observed in these cases (entries 5 and 6). The choice of
solvent turned out to be crucial for this reaction, as replacing DMSO
by other solvents, such as MeOH, EtOH, ClCH2CH2Cl, DMF, and
MeCN, resulted in inferior results (entries 7-11). Lastly, the control
Table 2. Scope of alkenyl aldehydesa
experiment
showed
that
the
photoredox
catalyst
O
Ir(ppy)2(dtbbpy)PF6 is essential for the acylarylation reaction (entry
12).
CHO
Ir(ppy)2(dtbbpy)PF6
R1
+ Ph2IPF6
Ph
R1
n
white LED, DMSO, rt
R2
Table 1. Evaluation of reaction conditionsa
R2
1
2a
3
O
Cl
O
O
Cl
Ph
Ph
Ph
Ph
Cl
3d
3b
3c
, 76%
, 72%
, 68%
O
Entry Catalyst
2
Solvent
Yield (%)
16
Br
O
O
1
Ru(bpy)3Cl2
Ir(ppy)3
Ph2IPF6/2a DMSO
Ph2IPF6/2a DMSO
2
23
Ph
Ph
Ph
Ph
MeO2C
F
3
Ir(dF(CF3)ppy)2(dtbbpy)PF6 Ph2IPF6/2a DMSO
52
3e
, 83%
3f
3g
, 82%
, 76%
O
4
Ir(ppy)2(dtbbpy)PF6
Ir(ppy)2(dtbbpy)PF6
Ir(ppy)2(dtbbpy)PF6
Ir(ppy)2(dtbbpy)PF6
Ir(ppy)2(dtbbpy)PF6
Ir(ppy)2(dtbbpy)PF6
Ir(ppy)2(dtbbpy)PF6
Ir(ppy)2(dtbbpy)PF6
/
Ph2IPF6/2a DMSO
Ph2IBF4/2b DMSO
Ph2IOTf/2c DMSO
Ph2IPF6/2a MeOH
Ph2IPF6/2a EtOH
70
O
O
O
5
55
O
MeO
6
40
Ph
Ph
Ph
7
62
3h
3i
, 67%
3j
, 74%
O
, 50%
O
8
19
O
9
Ph2IPF6/2a ClCH2CH2Cl Trace
10
11
12
Ph2IPF6/2a DMF
Ph2IPF6/2a MeCN
Ph2IPF6/2a DMSO
7
Ph
Ph
Trace
0
Et
OMe
, 64%
b
b
b
3k
3l
, 80%
3m
, 74%
O
a Reaction conditions: 1a (0.25 mmol), 2 (0.75 mmol), catalyst (2 mol%), solvent
(2 mL), white LED, 25 oC, 36 h. Yields of the isolated products are given.
O
O
Ph
Ph
Ph
With the optimized reaction conditions in hand, we examined the
structural diversity of substrates 1 by assessing the substitution
effect on them, and the results are summarized in Table 2.
Chlorinated aldehydes 1b, 1c, and 1d afforded the corresponding 2-
benzyl indanones 3b, 3c, and 3d in respective yields of 76%, 72%,
and 68%, suggesting that the substitution pattern has no significant
impact on the reaction. Remarkably, the substrate 1g, with a strong
electron-withdrawing group (CO2Et) on the benzene ring, was
smoothly converted into the desired indanone 3g in 82% yield.
Since electron-deficient benzenes are poor substrates for the
Friedel-Crafts acylation, our method provides a good alternative
protocol for the access of this type of compounds. In contrast to our
previous report that was enabled by the base-promoted
epimerization,11e this reaction displayed excellent trans-
diastereoselectivity (dr > 98:2) under the base-free conditions.
Specifically, the reaction of 1k-1m exclusively afforded trans-2,3-
3o
, 36%
3p
, trace
3n
, 82%
O
O
O
Ph
Ph
N
EtO2C CO2Et
Ts
3q
3r
3s
, 60%
, 66%
O
, 63%
O
n-Pr
n-Pr
Ph
Ph
O
, trace
3t
3u
, trace
a
Reaction conditions: 1 (0.25 mmol), 2a (0.75 mmol), Ir(ppy)2(dtbbpy)PF6 (2
mol%), DMSO (2 mL), white LED, 25 oC, 36 h. Yields of the isolated products are
given. b dr > 98:2.
2 | J. Name., 2012, 00, 1-3
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Subsequently, various diaryliodonium hexafluorophosphates
The resultant product 3a was subjected to further modification
were tested under the optimal reaction conditions. As shown in (Scheme 2). Using 1.7 equiv of HIO3 as the oxidant,15 it was
Table 3, diaryliodonium salts bearing different halogen atoms such smoothly converted into 2-benzyl-1H-inden-1-one (5a) in 60% yield.
as Cl, Br, and F were viable substrates for this reaction (4a-4d), Additionally, the ketone olefination was also feasible, as
which may be used for further synthetic elaborations through demonstrated by the facile synthesis of compound 5b via the Wittig
transition-metal-catalyzed cross-coupling reactions. The reaction of reaction.
electron-rich substrate 2j and electron-poor one 2k afforded the
To gain some insights into the reaction pathway, we conducted a
desired products 4g and 4h in 76% and 71% yield, respectively,
few control experiments. In the presence of 3 equiv of the radical
implying that the electronic effect of diaryliodonium
scavenger
2,2,6,6-tetramethylpiperidinooxy
(TEMPO),
the
hexafluorophosphates has little influence on the reaction.
Gratifyingly, the substrate 2l, possessing a NO2 group on the
benzene ring, was also effective for the indanone formation (4i).
Unfortunately, diheteroaryliodoniums were incompatible for this
reaction (4j and 4k).
formation of 3a was completely inhibited, and instead, the TEMPO-
adduct 6a could be detected by HRMS analysis (eq 1). Additionally,
the radical clock experiment with (1-cyclopropylvinyl)benzene as
the radical probe led to a ring-expanded product 6b in 35% yield (eq
2). These results indicated that the formation of phenyl radical may
be involved in the catalytic cycle.
Table 3. Scope of diaryliodonium hexafluorophosphates a
O
As such, a possible mechanism has been proposed in Scheme 3
for this photocatalytic acylarylation of unactivated alkenes. Initially,
the reduction of diaryliodonium salts 2 with a photoexcited Ir(III)*
species produces the aryl radical A, accompanied by the generation
of an Ir(IV) intermediate. Trapping the aryl radical A with the C-C
double bond of 1 followed by an intramolecular addition to
aldehyde delivers an alkoxy radical C, which can be transformed to
an α-hydroxy carbon radical D via a formal 1,2-hydrogen atom
transfer (1,2-HAT).16 Afterward, the SET oxidation of D by Ir(IV)
furnishes the corresponding products 3 or 4 with concurrent
formation the Ir(III) catalyst, a precursor for the photoexcited Ir(III)*
species.
CHO
Ir(ppy)2(dtbbpy)PF6
+ Ar2IPF6
white LED, DMSO, rt
Ar
1a
2
4
O
O
O
4a
, 70%
4b
4c
, 81%
, 74%
Cl
Br
F
O
O
O
F
4d
4e
4f
, 70%
, 79%
, 55%
O
O
standard conditions
TEMPO
CHO
Ph
O
O
Ph2IPF6
+
+
+
PhOTEMP
6a, detected
by HRMS
(1)
(2)
1a
1a
2a
3a, 0%
Ph
Ph
O
CHO
Ph
+
4g
4h
4i
, 62%
standard conditions
, 76%
, 71%
OMe
CO2Et
NO2
Ph2IPF6
O
O
2a
3a, 0%
6b, 35%
CHO
R1
1
S
N
4j
, trace
4k
, trace
CHO
R1
R2
Ar2IPF6
Ar
A
2
Ar
Ar
a
Reaction conditions: 1a (0.25 mmol), 2 (0.75 mmol), Ir(ppy)2(dtbbpy)PF6 (2
B
R2
mol%), DMSO (2 mL), white LED, 25 oC, 36 h. Yields of the isolated products are
SET
given.
O
OH
*[IrIII]
[IrIV
]
O
O
O
1,2-HAT
Ar
R1
R1
Ph
Ph
HIO3 (1.7 equiv)
DMSO, 50 o
R2
R2
Bn
Bn
C
D
C
SET
3a
3a
5a
, 60%
O
hv
[IrIII]
+ H+
Ar
R1
Ph3P=CH2 (1.2 equiv)
THF, rt
R2
3
4
or
5b
, 65%
Scheme 3 Possible mechanism.
Scheme 2 Transformation of 3a
.
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In conclusion, we have developed
a novel photocatalytic
acylarylation of unactivated alkenes using diaryliodonium
hexafluorophosphates as the arylation reagent, thus generating a
variety of 2-benzyl indanones, 3,4-dihydronaphthalen-1(2H)-ones,
and 2,3-dihydroquinolin-4(1H)-ones in promising yields at room
temperature. trans-2,3-Disubstituted indanones can be exclusively
synthesized via this protocol. The mild reaction conditions, high
efficiency, broad substrate scope, and excellent diastereoselectivity
enable it a very attractive method for the fast construction of
biologically active molecules including indanones. This reaction
represents a new type of alkene acylarylation featuring the tandem
radical arylation/acylation. It permits the successful transformation
of unactivated alkenes, thus providing a good complementary
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ChemComm
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DOI: 10.1039/C8CC02636J
A photocatalytic acylarylation of unactivated alkenes using diaryliodonium salts is
described, giving 2-benzyl indanones and related compounds in promising yields with
excellent diastereoselectivity.