One-Pot Tandem Photoredox and Cross-Coupling Catalysis with a Single Palladium Carbodicarbene Complex

Article abstract of DOI:10.1002/anie.201800951

The combination of conventional transition-metal-catalyzed coupling (2 e^? process) and photoredox catalysis (1 e^? process) has emerged as a powerful approach to catalyze difficult cross-coupling reactions under mild reaction conditions. Reported is a palladium carbodicarbene (CDC) complex that mediates both a Suzuki–Miyaura coupling and photoredox catalysis for C?N bond formation upon visible-light irradiation. These two catalytic pathways can be combined to promote both conventional transition-metal-catalyzed coupling and photoredox catalysis to mediate C?H arylation under ambient conditions with a single catalyst in an efficient one-pot process.

Full text of DOI:10.1002/anie.201800951

A Journal of the Gesellschaft Deutscher Chemiker
Angewandte
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Accepted Article
Title: One-Pot Tandem Photoredox and Cross-Coupling Catalysis with
a Single Pd-Carbodicarbene Complex
Authors: Tiow-Gan Ong, Yu-Chen Hsu, Vincent C.-C. Wang, Ka-Chun
Au-Yeung, Chung-Yu Tsai, Chun-Chi Chang, Bo-Chao Lin,
Yi-Tsu Chan, Chao-Ping Hsu, Glenn P. A. Yap, and Titel
Jurca
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201800951
Angew. Chem. 10.1002/ange.201800951
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10.1002/anie.201800951
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One-Pot Tandem Photoredox and Cross-Coupling Catalysis with
a Single Pd-Carbodicarbene Complex
Yu-Chen Hsu[a,b], Vincent C.-C. Wang*[a,c], Ka-Chun Au-Yeung[a], Chung-Yu Tsai[a], Chun-Chi Chang[a],
Bo-Chao Lin[a], Yi-Tsu Chan[b], Chao-Ping Hsu[a], Glenn P. A. Yap[d], Titel Jurca*[e], Tiow-Gan Ong*[a,f]
Abstract: The combination of conventional transition metal-
catalyzed coupling (2e- process) and photoredox catalysis (1e-
process) has emerged as a powerful approach to catalyze difficult
cross-coupling reactions under mild conditions. We report a Pd-
carbodicarbene (CDC) complex that mediates both Suzuki-Miyaura
coupling and photoredox catalysis for C-N bond formation upon
visible-light irradiation. These two catalytic pathways can be
combined to promote both conventional transition-metal-catalyzed
coupling and photoredox catalysis to mediate C-H arylation under
ambient conditions with a single catalyst in an efficient one-pot
process.
conventional cross-coupling catalysts (e.g. Ni or Pd) alone.[8a, 8h, 8i]
The key development common to these reports is the utilization of
visible-light driven catalysis as a bridge to induce the desired redox
process.[7b, 8h]
We sought to create a single component organometallic
catalyst that can promote these two distinct processes (i.e.
reactions at both the ground state (2e- process) and excited
state (1e- process)). Promoting tandem reactions in a one-pot
manner as described in Scheme 1B circumvents the need for
extra photoredox catalysts to act as photosensitizers (vide
supra). Single catalyst systems also negate potential
incompatibility which can arise from a multiple catalyst approach.
[10]
Additionally, one-pot processes operating on fewer
Carbodicarbenes (CDCs) are carbones (CL2) that feature
a
components inherently simplify subsequent reaction and
purification steps, reducing both time, reagents, and solvents
used which is both economically and environmentally
beneficial.[11]
dicoordinated central carbon (C0) bearing two lone pairs of electrons
with N-heterocyclic carbenes (NHCs) as ligands (L).[1] Due to the two
lone pairs on the central carbon, CDCs have been implicated as
strong -donating complementary surrogates to the well-established
NHCs. To date, though CDC-promoted transition metal catalysis is
still in its infancy, efforts have yielded encouraging results in
[2-5]
catalysis.
As with their NHC counterparts, the recurring theme in
the reactions promoted by CDC-based species, to date, involves a
2e- process. In the context of cross-coupling reactions, this is not
only true of NHC/CDC-based species, but of transition metal
catalysts in general (Scheme 1).[6] However, the conventional
transition-metal-catalyzed cross-coupling methodology based on the
2e- process, where organometallic catalysts are at the ground-state
oxidation level, can be prone to inherent limitations; e.g. the
formation of Csp3-Csp3 or Csp3-Csp2 bonds, which often requires
additional chemical manipulations.[7]
The emerging area of visible-light photoredox using excited-state
organometallics has facilitated significant advancement in organic
8]
synthesis via 1e- processes under benign conditions.[7a,
Concomitantly, the seminal works on merging conventional cross-
coupling and photoredox catalysis have also led to a spin-off
synthetic paradigm (Scheme 1A). Within this regime, photoredox
catalysts (e.g. Ru or Ir species) play a secondary role in the cross-
coupling reaction by generating radical intermediates to subdue a
specific high-energy step.[9] This would be difficult to achieve by
[a]
Y.-C. Hsu, V. C.-C. Wang, K.C. Au-Yeung, C.-Y. Tsai, C.-C. Chang,
B.-C. Lin, Prof. C.-P. Hsu, Prof. T.-G. Ong; Institute of Chemistry,
Academia Sinica, Taipei 11529, Taiwan, Republic of China
E-mail: tgong@gate.sinica.edu.tw
[b]
[c]
[d]
[e]
Y.C. Hsu, Prof. Y.-T. Chan, Department of Chemistry, National
Taiwan University, Taipei 10161, Taiwan, Republic of China
V. C.-C. Wang, Department of Chemistry, Ångström Laboratory,
Uppsala University, Uppsala 75120, Sweden
Prof. G. P. A. Yap, Department of Chemistry and Biochemistry,
University of Delaware, Newark, Delaware, 19716, USA
Prof. T. Jurca, Department of Chemistry & Cluster for the Rational
Design of Catalysts for Energy Applications and Propulsion,
University of Central Florida, Orlando, Florida 32816, USA
Prof. T.-G. Ong, Department of Applied Chemistry, National Chiao
Tung University, Hsinchu 300, Taiwan, Republic of China
Scheme 1. Strategies for the combination of catalytic photoredox and
transition-metal-based coupling reactions. (A) Utilizing two distinct catalysts to
promote photoredox and cross-coupling. (B) Proposed alternative strategy
promoted by a single pre-catalyst. M, N = metal center; X,Y = leaving groups.
With this in mind, we turned our attention to Pd-based
complexes with square planar geometry. Such species have
been widely used as catalysts for cross-coupling reactions[6], yet
are structurally distinct from the six-coordinate species (e.g.
[f]
Supporting information for this article is given via a link at the end of the
document.
2+
Ru(bpy)3 and Ir[dF(CF3)ppy]2(dtbbpy)+) conventionally used as
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10.1002/anie.201800951
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COMMUNICATION
photoredox catalysts.[7a] Although second or third row transition
metal complexes can greatly increase spin-orbital coupling to
yield the long-lived triplet excited state, the excited state of d8
organotransition-metal complexes (Pd(II)) generally have a
shorter lifetime due to the thermal deactivation through low-lying
d-d states.[12] Such obstacles can be minimized through judicious
ligand design; strong σ-electron donation from the ligand can
raise the energy of the low-lying d-d states in Pd species.[12b]
Pincer-type ligands can provide the rigid scaffold needed to
minimize structural distortion of the excited state.[12b, 13]
complexes 4 and 5 showed lower activities under similar
conditions.
With optimized conditions in hand, we expanded the scope
of aromatic aldehydes 6x reacted with pyrrolidine 7a in the
presence of 3 (Table 1). The aromatic aldehydes (6a-d & f)
bearing electron-withdrawing substituents (p-Cl, p-CN, p-NO2, o-
NO2, p-CF3) led to high yields of product 8a-d and f (75-91%).
The yield of p-methyl substituted aromatic aldehyde 6e was
lower (41%). Encouragingly, most electron withdrawing and
donating groups at the meta position (6g-j) proved suitable,
ultimately resulting in good yields (55-70%). Aromatic aldehyde
derivatives such as isonicotinaldehyde (6k), 2-naphthaldehyde
(6l) and [1,1'-biphenyl]-4-carbaldehyde (6m) were also feasible.
Under these guidelines, a Pd species bearing the strong
electron-donating framework of bis-py-CDC[4] emerged as a
compelling candidate to promote both 1- and 2-e- processes.
Herein we demonstrate that in addition to conventional Suzuki
and Heck cross-coupling[4], this molecular framework can also
mediate photochemical C-N coupling under mild conditions[14]
15]
and C-H arylation without additional photosensitizers.[9a,
These can be incorporated to facilitate cascade reactions for C-
N and C-C cross coupling in an orthogonal process at a single
Pd-center (Scheme 1B).
Scheme 2. (A) CDC Pd complex 3 and its analogues 4 and 5. (B) Optimization
of photo-mediated C-N coupling of 6a and 7a.
Table 1. Scope of photoredox reaction for aldehydes and amines.
The substrate scope was then expanded to secondary
amines with p-nitro-benzaldehyde 6c. Excellent-to-moderate
yields were obtained with various sizes of cyclic amines (8c, 9a
& 9b) such as pyrrolidine, piperidine and azepane. The protocol
proved effective for five and six-membered cyclic amine
derivatives (7c-e) with moderate yields (56-75%). Good
reactivity (73%) was seen in morpholine (7f), but 1-
methylpiperazine (7g) displayed lower conversion (32%). Finally,
acyclic amine dibenzylamine resulted in a yield of 76% 9h,
which was markedly better than its counterpart diallylamine 9i
(29%).
It is estimated that more than 25% of medicinal synthetic
protocols at some stage involve amide bond-forming process.[16]
As such, the formation of amides is a central focus in organic
[17]
synthesis for natural products and drug development.[16]
Photoredox-driven reactions provide a compelling, “mild” route
to C-N bond formation. We attempted a photoredox reaction of
4-chlorobenzaldehyde 6a and pyrrolidine 7a with complexes 3, 4
and 5 (Scheme 2). Details on the preparation of 3, 4 and 5 can
be found in SI. The coupling reaction proceeded to 91 % yield of
amides 8a in 16 h when 3 equiv. of amines and 1 equiv. of aryl
aldehydes in DMF solution were employed under irradiation of a
23 W household fluorescent light bulb. The optimum catalyst
loading of 3 was found to be ca. 0.5 mol %. Analogous Pd
To further delineate the photoredox mechanism of C-N
coupling with 3, we performed spectroscopic and
electrochemical measurements. The UV-visible spectrum of 3
revealed a strong absorption peak at 499 nm. This corresponds
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10.1002/anie.201800951
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to observed C-N coupling activity only under green and blue
LED irradiation, but not red (Figure 1i). Time-Dependent DFT
calculations suggest that the low-energy absorption is ascribed
to the intra-ligand charge transfer and metal-to-ligand charge
transfer excitations. (Figure S8). An emission peak was
observed at 570 nm when samples of 3 were excited at 499 nm,
while cyclic voltammetry revealed a reversible redox couple
peak for Pd(III)/Pd(II) around E1/2 = 0.87 V (all potentials
reported herein are against the saturated calomel electrode,
SCE, Figure 1ii). Therefore, the reduction potential of the
excited-state of 3* (Pd(III)/Pd(II)*) is approximate E= -1.31 V
formation of paramagnetic 3 (Pd(III)). After adding pyrrolidine
amine to the sample, the sharp NMR pattern reappeared,
consistent with the regeneration of a Pd(II) species. Based on
the sum of these observations, we propose a photoredox
reaction mechanism as summarized in Figure 1iii: First, the
superoxide radical is generated from O2 via oxidative quenching
of the excited state of Pd(II)* to Pd(III). Subsequently, the amine
acts as an electron donor in the catalytic cycle to regenerate the
reduced species 3 accompanied by H2O2 formation. The acetal
or aminal adducts (A) result from nucleophilic attack of amine
with aldehyde. Adduct A is then oxidized by H2O2 to afford
desired product 8x.
(see SI for further information), which is lower than E= -0.81 V
2+ [7a]
for the redox couple, Ru(III)(bpy)33+/Ru(II)*(bpy)3
.
Figure 1. (i) The UV-visible (black) and emission (blue, excited at 499 nm)
spectra of 3 in DMF. (ii) Cyclic voltammogram of 3 (0.1 mM) in DMF and
ferrocene (0.1 mM) as internal standard, scan rate = 100 mV/sec. (iii)
Proposed photoredox mechanism for C-N bond formation.
Prior studies suggest that H2O2 facilitates the oxidative
amidation of aryl aldehydes.[14a, 18] As we found that O2 was
required for C-N coupling to occur, and the reduction potential of
∙-
excited 3* (-1.31 V) is more negative than E (O2/O2 ) = -0.87 V,
[19] it is likely that H2O2 may be a key intermediate in the process.
We propose that the excited state of 3* should react favorably
with O2 through an oxidative quenching process followed by
proton transfer from amines to generate H2O2 which was
detected by H2O2 test strips, when a mixture of 3 and pyrrolidine
was illuminated in the presence of O2 (Figure S3). During the
course of reaction, we observed that two equivalents of amines
were always required along with a moderate amount of imine
formed as byproduct (Figure S5). These observations hinted to
the likelihood that amine substrates not only serve as coupling
reagents, but may also play a crucial role as sacrificial
reductants. Closer examination of the reduction potential of
pyrrolidine (-0.015 V; Figure S6) suggests that oxidized complex
3(Pd (III)) could accept an electron from the more negative
amine derivatives. The role of amines was further investigated
and verified by NMR experiments. When illuminating 3 in the
presence of O2, the 1H NMR spectra become broad and altered
(aryl proton peaks broaden; Figure S7), suggesting the
Scheme 3. (A) Synergistic catalytic cycle based on single component 3. (B)
Scope of photoredox C-H Arylation.
Encouraged by the success of the visible-light promoted C-N
bond formation, we sought to explore the possibility that 3 may
also mediate other photoredox reactions. Recently, Sanford et al.
reported the development of directing group-directed C-H
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10.1002/anie.201800951
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arylation at room temperature with aryldiazonium salts.[9a] This
was achieved by merging two different catalytic sequences; Pd-
catalyzed C-H activation and Ru-mediated photoredox. We
reasoned that 3 could potentially promote such multi-component
reactions without additional photosensitizers like Ru(bpy)3Cl2.
Our proposed catalytic cycle is outlined in Scheme 3A. The key
aspect of this scheme is that the photo-excited Pd(II)* species is
able to react with aryldiazonium salt (E =~ 0 V)[20] to generate an
aryl radical which couples with complex I to participate in
conventional cross-couple reactions yielding the Ar-PhDG
coupling product. On the basis of this synergistic catalysis plan,
our investigation to delineate suitable reaction conditions
focused on C-H arylation of 2-(o-tolyl)pyridine 11a with p-
nitrophenyldiazonium tetrafluoroborate 10a (Scheme 3B).
Encouragingly, the desired C-H arylation product 12a was
formed with 96 % yield at room temperature in the presence of 5
mol % 3 using 23 W fluorescent light in conjunction with 0.2
equiv. of Ag2CO3 as additive. Other electron-deficient aryl
coupling reagents 10b-d performed similarly well. Electron-rich
substrates (10e & f) were tolerated, albeit 20 mol % catalyst
loading was required to achieve high conversion. Interestingly,
10g bearing both nitro and methoxy functional groups coupled
proficiently to deliver product 12g (92 % yield). Finally, we
focused on aryl substrates bearing directing groups. A diverse
array of electron-deficient phenyl pyridines with various
substituents (CF3, Cl, F and NO2, 11b-e) was shown to be
compatible with this approach. Phenylpyrimidine (11f) and
naphthalenyl-pyridine (11g) were also amenable to this
methodology affording products in the yield of 75% and 32 %,
respectively. Pyrrolidinone (11h) proved unsuitable, however,
pyrazole (11i) could be employed, but with reduced yields (47%).
Our studies reveal that 3 also enables broad scope Suzuki-
Miyaura C-C cross coupling between aryl-bromides and phenyl
boronic esters (see SI). Having established complex 3 as a
suitable catalyst for both photoredox and conventional cross-
coupling reactions individually, we shifted focus to the
development of a tandem, one-pot system (Scheme 4). In
method A, the C-C cross coupling reaction of 6x and aryl
boronic acid 14y was performed with isolation and purification of
its product 15x (~ 95 %) and subsequently used to examine the
photoredox-mediated amidation process with amines to afford
16xy. Method A would then serve as a benchmark to measure
the efficacy of method B (one-pot synthesis) ([total yield
B/overall yield A]x100%). In method B, a one-pot relay process
Scheme 4. Binfunctional catalysis based on C-C cross coupling and
photoredox C-N coupling reactions.
As part of our ongoing efforts to better understand, and expand
the scope of application for the CDC ligand framework, we
report a new type of bifunctional catalyst for cross-coupling
reactions based on two distinct mechanisms, a 2e- cross-
coupling and 1e- photoredox. The desired catalytic process is
modulated by visible light, and contrary to the prior art, does not
require additional photosensitizers. Most importantly, these two
distinct catalytic principles can operate within a single-catalyst
based one-pot tandem catalytic system. Our ongoing efforts
focus on improving these unique catalysts and the development
of new bond-forming protocols which exploit the tandem cross-
coupling and photoredox capabilities for the synthesis of value-
added compounds via one-pot reactions.
Acknowledgements
This work was financially supported by the Ministry of Science &
Technology of Taiwan (MOST-104-2628-M-001-005-MY4 grant)
and Academia Sinica Career Development Award (104-CDA-
M08). VW acknowledges financial support from Wenner-Gren
foundation. We are also grateful for suggestions from Prof. L.
Hammarström, Dr. E. Borbas, Mr. J. Föhlinger and Mr. B.
Johnson.
of 2.5-5 mol%
3
was capable of carrying out dual,
mechanistically-distinct reactions in a sequential fashion without
further purification and isolation of intermediates. The total yields
for 16a-d were 54%, 28%, 67% and 43%, respectively. Their
efficacy with respect to Method A is considered good (88-66%),
thus illustrating the possibility of one-pot sequential reactions
mediated by a single component Pd catalyst, which to our
knowledge is thus far unprecedented. The tandem reactions can
also be conducted in the reverse manner (i.e. photoredox
followed by Suzuki reaction). However, this sequence generally
led to lower yields, which we postulate is due to the
decomposition of catalysts under prolonged light exposure. The
addition of “fresh” catalyst to the reaction mixture prior to the
Suzuki step led to improved yields.
Keywords: carbones • cross-coupling • photocatalysis • tandem
reactions • one-pot synthesis • photoredox
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Entry for the Table of Contents
COMMUNICATION
Yu-Chen Hsu, Vincent C.-C. Wang*, Ka-
Chun Au-Yeing, Chung-Yu Tsai, Chun-
Chi Chang, Bo-Chao Lin, Yi-Tsu Chan,
Chao-Ping Hsu, Glenn P. A. Yap, Titel
Jurca*, Tiow-Gan Ong*
Page No. – Page No.
One-Pot Tandem Photoredox and
Cross-Coupling Catalysis with a
Single Pd-Carbodicarbene Complex
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