Visible-Light-Promoted Oxidative Alkylarylation of N-Aryl/Benzoyl Acrylamides Through Direct C?H Bond Functionalization

Article abstract of DOI:10.1002/adsc.201900712

Radical cascade oxidative alkylarylations of N-aryl/benzoyl acrylamides have been established through visible-light-enabled photocatalysis, furnishing a wide variety of functionalized oxindoles and isoquinolinediones in good-to-excellent yields under the

Full text of DOI:10.1002/adsc.201900712

Title: Visible-Light-Promoted Oxidative Alkylarylation of N-Aryl/Benzoyl
Acrylamides through Direct C-H Bond Functionalization
Authors: Shunyou Cai, Maojian Lu, Tao Zhang, Dabao Tan, Chengzhu
Chen, Ying Zhang, and Mingqiang Huang
This manuscript has been accepted after peer review and appears as an
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201900712
Link to VoR: http://dx.doi.org/10.1002/adsc.201900712

10.1002/adsc.201900712
Advanced Synthesis & Catalysis
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Visible-Light-Promoted Oxidative Alkylarylation of N-
Aryl/Benzoyl Acrylamides through Direct C-H Bond
Functionalization
Maojian Lu,a Tao Zhang,a Dabao Tan,a Chengzhu Chen,a Ying Zhang,a Mingqiang Huanga
and Shunyou Cai*a,b
a
Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry,
Chemical Engineering and Environment, Minnan Normal University, Zhangzhou, 363000, People’s Republic of China
b
Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School,
Peking University, Shenzhen, 518055, People’s Republic of China
E-mail: caishy05@mnnu.edu.cn
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
other heterocyclic compounds and natural products.[4]
Abstract: Radical cascade oxidative alkylarylations of N-
aryl/benzoyl acrylamides have been established through
visible-light-enabled photocatalysis, furnishing a wide
variety of functionalized oxindoles and isoquinolinediones
in good-to-excellent yields under the synergistic
interactions of an organic fluorophores-type photocatalyst
4CzIPN, trifluoroacetoxyiodobenzene (PIFA), and 1,3,5-
trimethoxybenzene with visible light irradiation. The
prominent features of this method are the broad substrate
scope, excellent functional group tolerance, and mild
reaction conditions.
Over the past years, although multitudinous
approaches[5] have been disclosed to prepare these
structures, most of them still notably require multiple
steps, use of toxic metal salts, and strong oxidants under
high reaction temperatures or microwave stimulations.
In this paper, we anticipated that the C-H activation
strategy relying on photoredox catalysis might be
served as an alternative and efficient scenario for
construction of functionalized oxindoles and
isoquinolinediones, in which simple and readily
available acetonitrile, acetone and dimethyl sulfoxide
could be directly employed as coupling partners under
mild reaction conditions.
Keywords: Photocatalysis; visible light; alkylarylation;
nitrogenous heterocycles; C-H functionalization
Direct functionalization of the inert sp3 C-H bond has
emerged as a powerful synthetic technology in modern
synthetic organic chemistry, bringing about a variety of
organic transformations including diverse C-C, C-N,
Scheme 1. Visible-light-enabled C-H functionalization
strategy to nitrogenous heterocyclic substances.
and C-O bond formations.[1]
Considering the
environmental friendliness, reaction economic, and
operational simplicity, advance in this field still
requires further achievements in developing new
methods that can proceed smoothly under mild reaction
conditions. As a response to this challenge, visible-
light-enabled photoredox catalysis[2-3], with advantages
of abundant solar energy, simple operation, and
convenient reaction devices, is regarded as an effective
protocol; and such activities have been regularly
reviewed and updated. Not surprisingly, since most
organic compounds cannot absorb visible light, it
usually requires the participation of an appropriate
photocatalyst to access such processes.
Owing to our research program focusing on the
design and discovery of visible-light-enabled catalysis
methods for accessing valuable bioactive molecules,[6]
as shown in Scheme 1, we envisioned that the event of
a hydrogen abstraction might be initiated on the carbon
center adjacent to electron-withdrawing group under
synergistic actions of an organic photocatalyst, external
oxidant, and visible light irradiation, thereby leading to
a
relatively long-lived alkyl radical species.
Subsequently, the in-situ generated alkyl radical would
be intercepted by the C=C double bonds of acrylamide,
followed by a sequential process of cyclization-
oxidation-deprotonation, yielding the substituted
oxindoles and isoquinolinediones. Indeed, after
carefully screening the reaction conditions, a versatile
As a highly versatile class of frequently encountered
heterocyclic scaffolds, oxindoles or isoquinolinediones
are known to function as useful precursors to synthesize
1
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10.1002/adsc.201900712
Advanced Synthesis & Catalysis
and efficient protocol was eventually set up to prepare characteristics. Furthermore, a series of hypervalent
oxindoles and isoquinolinediones.
iodine compounds (entries 7-10), including PhI(OAc)2
(PIDA), acetoxybenziodoxole (BI-OAc),
Table 1. Conditions survey for the cyano substituted
oxindole formation.
hydroxybenziodoxole (BI-OH), and 2-iodoxybenzoic
acid (IBX), were found to have negative effects on
cyano substituted oxindole formation. Addition of other
solvents only resulted in drastically inhibiting the
reactivity (entries 11-12). Further trials utilizing eosin
Y, Ru(bpy)3Cl2, or Ir(ppy)2(dtbpy)PF6 (Ir-cat. 1) as an
alternative photocatalyst all led to lower yields of the
desired products (entries 13-15). Finally, there was no
reaction in the absence of an oxidant, a photocatalyst, or
visible light, which unambiguously manifested that all
of them were requisite for this transformation (entries
16-18).
a) [Ir-cat.] = Ir[dF(CF3)ppy]2(dtbpy)PF6. b) No light. c) 4CzIPN
d)
= 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene. PIFA
=
PhI(OCOCF3)2; PIDA
=
PhI(OAc)2; BI-OH
=
e)
hydroxybenziodoxole; BI-OAc = acetoxy-benziodoxole.
Yield of isolated product.
Scheme 2. Reactivity screening of the substituent R1.
To verify the feasibility of initial anticipation, we
began our investigation by employing N-methyl-N-(p-
tolyl)-methacrylamide 1a as model substrates under
photocatalytic conditions (Table 1). When the reaction
was performed in acetonitrile (ACN) utilizing 1,2,3,5-
tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN)[7]
as the photocatalyst, no anticipated product was
detected in the presence of stoichiometric amounts of
hypervalent iodine(III) compound[8] PhI(OCOCF3)2
(PIFA) under blue LEDs irradiation (entry 1, Table 1).
Gratifyingly,
a
significant
observation
was
subsequently noted that the desired cyano substituted
oxindole 2a could be produced in 61% yield when 1.5
equiv of 1,3,5-trimethoxybenzene (A) was employed as
the additive (entry 2). Further increasing the amount of
1,3,5-trimethoxybenzene and PhI(OCOCF3)2 to 2.0
equiv, it was capable of improving the desired product
2a up-to a good yield (82%, entry 3). Other similar less
nucleophilic additives, such as 1,3-dimethoxybenzene
(B), anisole (C), and 1,3,5-trimethylbenzene (D) were
investigated (entries 4-6), but all pointed to either a
lower product yield or almost total suppression in
reactivities. So we believed that the efficient promoting
effect of 1,3,5-trimethoxybenzene additive possibly
Scheme 3. Reactivity screening of substituents R2 and
R3.
Using the optimized reaction conditions, a variety of
substrates carrying diverse substituent groups on N-aryl
moiety were subjected to this visible-light-enabled
originated
from its
strong electron-donating
2
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10.1002/adsc.201900712
Advanced Synthesis & Catalysis
oxidative alkylation protocol to explore its substrate products could be obtained in comparable yields
generality, and the results were shown in Scheme 2. (Scheme 5).[10] Furthermore, structurally functionalized
Interestingly, compared with the substrate 1a, the oxindoles assembled by this method are amendable for
presence of a methyl group at the ortho-position in the further structural elaborations. For example, cyano
substrate 1b seemed to retard the transformation to substituted oxindole 2a was conceivably converted into
some extent owing to the steric-bulk effect (37% yield). tricyclic indoline 12 by a two-steps modification
The aryl ring sizes appeared to have little influence on including reductive amination and acetylation.[11] These
the reactivities (1c and 1d). However, the reaction observations, in conjunction with the above-mentioned
decomposition was detected with the substrate 1e reactivities, have demonstrated the practicality of the
bearing a strong electron-donating group on the method for accessing nitrogenous heterocyclic
aromatic ring. Notably, a range of the frequently substances with versatile functionalities.
encountered functional groups, such as the halogen
atoms (2f-2j), trifluoromethyl (2k), cyano (2l), carbonyl
(2m and 2n), sulfonyl (2o), and nitro (2p) group, were
demonstrated to be well-tolerated in this transformation
in terms of isolated yields (36-93%), thereby affording
a significantly versatile platform for further required
synthetic editing.
To further extend the substrate scope for this
photocatalytic protocol, we next examined a series of
N-aryl acrylamides bearing different variations on the
R2/R3 to react with acetonitrile under the optimal
condition. All of the substrates could smoothly undergo
this process to afford the desired products 4a-4l in
moderate-to-excellent yields (Scheme 3). The substrates
containing acyl (3a), aryl (3b), and alkyl (3c-3e)
substituents on the N atom (R2) were revealed to be
Scheme 5. Further survey of reaction scopes and
synthetic transformations.
readily implementable, thus giving the anticipated
products 4a-e in various yields (36-90%). Furthermore,
α-substituted olefins carrying different substituents,
such as ethyoxyl (3f), benzyl (3g), n-butyl (3h), and
phenyl (3i), were well accommodated, and the
corresponding products were obtained in 63-82% yields.
Notably, both tricyclic oxindoles (3j and 3k) and
heterocyclic oxindole (3l) also reacted effectively to
deliver the corresponding products in good yields.
Stimulated by the above results, we further apply this
established protocol to investigate the preparations of
cyano substituted isoquinolinediones 6, which are
significant heterocyclic structural motifs present in
numerous pharmaceuticals and agrochemicals.[9] As
depicted in Scheme 4, the observed reactivities
appeared to be quite general, since their corresponding
isoquinolinediones 6 were all consistently generated in
moderate-to-excellent yields.
To understand the potential reaction pathways, a
sequence of mechanistic experiments were carried out,
and the results were outlined in Scheme 6. In the model
reaction, accompanying 2a was the formation of 2-
iodo-1,3,5-trimethoxybenzene 13 as the major
byproduct, arising apparently from iodination of the
additive 1,3,5-trimethoxybenzene. Further studies
showed that 1,3,5-trimethoxybenzene could smoothly
react with PhI(OCOCF3)2 to afford a new hypervalent
iodine(III) reagent 15, which was also able to furnish 2-
iodo-1,3,5-trimethoxybenzene 13 only with
a
photocatalyst and visible light irradiation. Treatment of
N-aryl acrylamide 1a with the new generated
hypervalent iodine(III) reagent 15 in acetonitrile under
Scheme 4. Cyano substituted isoquinolinedione 6
syntheses.
Finally, it is interesting that when acetone or
dimethyl sulfoxide was used in place of acetonitrile
under otherwise identical reaction conditions, the
desired corresponding isoquinolinedione or oxindole
Scheme 6. Experimental probes on reaction mechanism.
3
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10.1002/adsc.201900712
Advanced Synthesis & Catalysis
otherwise identical reaction conditions, could provide Experimental Section
the oxindole 2a in 74% yield. Complete inhibition in
anticipated reactivity was observed when the radical
scavenger 2,2,6,6-tetramethyl-1-piperidinyloxy
A flame-dried round bottom flask was equipped with
magnetic stir bar and charged with N-aryl acrylamides
(0.159 mmol, 1.0 equiv), PhI(OCOCF3)2 (0.317 mmol,
2.0 equiv), 1,3,5-trimethoxybenzene (0.317 mmol, 2.0
(TEMPO) was introduced to the reaction system,
implying that the reaction should be a radical pathway.
Subsequently, a distinct kinetic isotope effect (KH/KD =
3.2) was recorded in this transformation, providing
straightforward evidence that C-H bond cleavage event
might be the rate-determining step. Finally, a range of
fluorescence quenching (Stern-Volmer) experiments
were conducted to comfirm which substance in the
reaction quenched the excited photocatalyst (see the
Supporting Information). The collected results revealed
that the excited photocatalyst should engage in single
electron transfer with the hypervalent iodine(III)
compound 15.[12]
equiv),
1,2,3,5-tetrakis(carbazol-9-yl)-4,6-
dicyanobenzene (4CzIPN) (0.0032 mmol, 0.02 equiv),
and ACN (8.0 mL). The reaction mixture was degassed
by purging thoroughly with nitrogen for 10 minutes,
then irradiated by blue LEDs (18 W) under a balloon
nitrogen atmosphere at room temperature until the
starting material disappeared from the TLC. After that
the reaction mixture was directly concentrated under
reduced pressure and the crude product was purified by
silica gel column chromatography using hexane/EtOAc
(4/1 to 2/1) to afford the desired product.
The above observed reactivities, incorporating with
previous literature,[5] collectively point to a plausible
mechanistic rationale illustrated in Scheme 7. 1,3,5-
trimethoxybenzene was first to react with
PhI(OCOCF3)2 to deliver the diaryliodonium salt 15,
which would undergo single electron transfer with
excited photocatalyst, thus generating the active iodanyl
radical E. Subsequently, a hydrogen on carbon center
adjacent to electron-withdrawing group would be
abstracted by the iodanyl radical E to provide the key
alkyl radical and 2-iodo-1,3,5-trimethoxybenzene 13.
Finally, radical addition would take place on N-aryl
acrylamide 1, followed by a sequential cyclization-
oxidation-deprotonation process, to lead to the
formation of the final substituted oxindole product, 2.
Acknowledgments
We thank the National Natural Science Foundation of
China (No. 21502086, and No. 41575118), Natural
Science Foundation of Fujian Province (No.
2019J01744), Outstanding Youth Science Foundation
of Fujian Province (No. 2015J06009), and Program for
Excellent Talents of Fujian Province for financial
support.
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4
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10.1002/adsc.201900712
Advanced Synthesis & Catalysis
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10.1002/adsc.201900712
Advanced Synthesis & Catalysis
COMMUNICATION
Visible-Light-Promoted Oxidative Alkylarylation
of N-Aryl/Benzoyl Acrylamides through Direct C-
H Bond Functionalization
Adv. Synth. Catal. 2019, 361, 1-5
M. Lu, T. Zhang, D. Tan, C. Chen, Y. Zhang, M.
Huang, S. Cai*
6
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