Cobalt-catalysed C-H carbonylative cyclisation of aliphatic amides

Article abstract of DOI:10.1039/c6sc05581h

A cobalt-catalysed C-H carbonylation of aliphatic carboxamide derivatives is described, employing commercially available Co(ii)-salts in the presence of a silver oxidant. This operationally simple process utilises an atmospheric pressure of CO and generates a range of substituted succinimide products bearing diverse functional groups that can be successfully accessed via this methodology.

Full text of DOI:10.1039/c6sc05581h

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Cobalt-catalysed C–H carbonylative cyclisation of aliphatic amides
Patrick Williamson‡, Alicia Galvin‡ and Matthew J. Gaunt★
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
A cobalt- catalysed C–H carbonylation of aliphatic carboxamide derivatives is described, employing commercially available
Co(II)-salts in the presence of a silver oxidant. This operationally simple process utilises an atmospheric pressure of CO and
generates a range of substituted succinimide products bearing diverse functional groups that can be succesfully accessed
via this methodology.
www.rsc.org/
A. Coꢀcatalysed CꢀH carbonylation with CO gas
The development of novel transition-metal catalysed
processes for the selective functionalisation of C–H bonds is an
important challenge within synthetic chemistry, enabling
efficient and streamlined routes to complex scaffolds.1 Whilst
noble metals represent the most extensively explored catalyst
class for C–H activation, the development of low-cost, 1st-row
transition-metal alternatives is receiving considerable
attention.2 Cobalt was the first of these elements to be
investigated, with Murahashi et al. reporting a succesful
carbonylative cyclisation procedure of imine and azobenzene
substrates as early as 1955 (Scheme 1A).3 Since this seminal
report, strategies have been developed that directly employ
commercially available and bench stable Co(II) salts for C–H
activation reactions.4 Monoanionic, bidentate directing
groups,5 such as the 8-aminoquinoline group first utilized by
Daugulis, have been found to be essential for C–H activation to
occur via these oxidative reaction platforms, and are believed
to stabilise postulated high-valent Co-intermediates (Scheme
1A).6-8 Whilst this reactivity mode has been widely exploited
for the functionalisation of sp2-hybridised C–H bonds,
(1). Murahashi's work
1. Co2(CO)8 (11 mol%)
CO (100ꢀ200 atm)
220ꢀ230 ºC, 5ꢀ6 h
O
Ph
N
N
Ph
2. Oxidation
O
aromatic imine
(2). Daugulis’ work
Co(acac)2 (20 mol%)
Mn(OAc)3—2H2O (1 equiv),
NaOPiv (2 equiv),
O
O
N
N
H
CO (1 atm), air,
N
N
O
CF3CH2OH, rt, 16ꢀ60 h
aromatic quinolinamide
B. Coꢀcatalysed sp3 CꢀH functionalisation
(2 equiv)
H
R3
Co(OAc)2—4H2O (20 mol%),
Co(OAc)2 (10 mol%),
O
Ag2CO3 (3 equiv),
Ag2CO3 (2.5 equiv),
R1
R2
N
H
PhCO2Na (0.5 equiv),
TBAI (4 equiv), Na2CO3 (3 equiv),
PhꢀCF3, Py (2 equiv), 150 ºC
N
H
PhCl, 150 ºC
O
aliphatic
O
quinolinamide
R1
R2
N
(1). Ge's work
(2). Zhang's work R1
N
R2
N
N
R3
C. This work ꢀ Coꢀcatalysed sp3 CꢀH carbonylation
O
N
Co(acac)2 (10 mol%),
O
Ag2CO3 (3 equiv),
analogous
C(sp3)–H
activation
procedures
remain
N
H
N
PhCO2Na (1.5 equiv),
N
O
H
underdeveloped, with only two known examples reported to
date. Ge and co-workers described efficient intra- and
intermolecular amidation reactions,9a and the Zhang group
CO, PhCl, 160 ºC
carboxamide derivative
substituted succinimide
O
subsequently
developed
an
alkynylation/cyclisation
N
procedure,9b affording substituted pyrrolidinone products in
excellent yields (Scheme 1B).10 Both processes require the 8-
aminoquinoline directing group to promote efficient reaction.
Co
Xn
N
cobaltacycle
Scheme 1 A Co-catalysed C–H carbonylation strategy
Prompted by our interest in catalytic oxidative C–H
carbonylation reactions,10-12 we reasoned that its merger with
cobalt catalysis, guided by a pyridyl-derived auxiliary, would
provide a distinct platform for C(sp3)–H activation using earth
abundant metals. Herein, we report the development of an
oxidative Co-catalysed carbonylative cyclisation procedure of
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aliphatic quinolinamides to yield a range of substituted cobalt(II) salts were found to be successful pre-catalysts for C–
succinimide products (Scheme 1C). The reaction proceeds H carbonylation. Whilst a drop in efficiency was observed for
under atmospheric pressures of CO using operationally simple CoBr2, a modest increase in yield of 7a to 91% was observed
conditions and accommodates a variety of versatile functional upon employing Co(acac)2 (entries 13-14). Lowering the
groups. During the submission of our manuscript, an elegant catalyst concentration from 20 mol% to 10 mol% was tolerated
study was reported by Sundararaju and co workers, which by increasing the reaction temperature to 160 °C, allowing
detailed the same Co-catalyzed carbonylation process.13
succinimide 7a to be observed in 94% assay yield, which could
At the outset of our studies, we prepared a range of be isolated in 89% yield (entry 15). Reducing the catalyst
pyridyl-derived pivaloylamide substrates (Scheme 2A) and loading to 5 mol% did not aid the reaction, and lowering the
exposed then to reaction conditions based on Ge’s C–H amount of the silver salt in the reaction was deleterious to the
amidation process (Co(OAc)2, sodium benzoate and Ag2CO3 in yield (entries 16-18)
PhCl at 150 ˚C) under a CO atmosphere.9 We observed the
Table 1. Reaction optimisationa
formation of the desired C(sp3)-H carbonylation product in
only one of these cases (Scheme 2B); quinolinamide 1a was
converted to succinimide 7a with an 86% assay yield. The
failure of any of the substrates to undergo carbonylation
highlights an important role of the 8-aminoquinoline group in
controlling the C–H activation.
Yield
(%)b
86
Entrya
Co, mol%
Base
Oxidant
T °C
A. Initial substrates synthesised and tested
O
O
Me Me
O
1
2
Co(OAc)2
Co(OAc)2
Co(OAc)2
Co(OAc)2
No Co
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
NaOAc
Ag2CO3
Ag2CO3
Ag2CO3
Ag2CO3
Ag2CO3
Ag2CO3
Ag2CO3
Ag2CO3
150
140
135
130
150
150
150
150
Me
Me
Me
Me
Me
Me
N
H
N
H
N
N
H
72
40
18
0
Me
N
Me
N
H
1a
2
3
3
O
4
O
O
Me
Me
Me
Me
Me
Me
Me
N
H
5
N
H
N
N
H
N
O
Me
Me
Me
6
Co(OAc)2
Co(OAc)2
Co(OAc)2
Co(OAc)2
Co(OAc)2
Co(OAc)2
Co(OAc)2
CoBr2
23
3
4
5
6
7
Na2CO3
B. Lead experiment
8
Na3PO4
2
Co(OAc)2 (20 mol%),
Ag2CO3 (3 equiv),
O
Me
Me
O
9
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
PhCO2Na
Mn(OAc)3. 150
6
Me
Me
N
N
H
10
11
12
13
14
15
16
17
18
NaClO3
CAN
150
150
150
150
150
160
160
160
160
3
PhCO2Na (1.5 equiv),
N
O
N
H
CO, PhCl,150 ºC, 24 h
6
1a
7a, 86%
No Ag
0
Ag2CO3
Ag2CO3
Ag2CO3
Ag2CO3
2.0 equiv
1.5 eqiuv
10
91
94
88
78
72
Co(acac)2
10 mol%
5 mol%
Scheme 2 Investigation of substrate structure and lead reaction
Next, we extensively assessed the reaction parameters of the
successful process with the aim of further improving the yield
as well as better understanding the role of each of the
components. We found that a temperature of at least 150 ˚C
was responsible for an effective reaction, with the yield of the
process dramatically reduced upon lowering the temperature
by only 15 ˚C (Table 1, entries 1-4). In the absence of the Co(II)
catalyst, C–H carbonylation did not proceed, confirming the
role of the metal species in mediating this process (entry 5).
Replacement of sodium benzoate base with sodium acetate,
sodium carbonate or sodium phosphate proved detrimental to
the efficiency of the process, with succinimide 7a being
formed in diminished 23%, 3% and 2% yield, respectively
(entries 6-8). Surprisingly, we found that silver salts were
essential for a successful reaction; only traces of the desired
product were observed upon replacing Ag(I) oxidants with
Mn(OAc)3.2H2O (entry 9), and complete loss of reactivity was
observed when alternative inorganic oxidants were employed
5 mol%
5 mol%
a Starting Reaction conditions: substrate 1 (0.2 mmol), Co source (10 mol%),
Base (1.5 equiv), Oxidant (3.0 equiv), PhCl (2 mL), CO (1 atm), 21 h. bThe
yield was determined by 1H NMR analysis of the crude reaction mixture
using 1,1,2,2-tetrachloroethane as the internal standard.
With a set of optimal conditions in hand, we next assessed
the scope of the Co-catalyzed C–H carbonylation reaction. We
found that simple alkyl-derived carboxamides were effective
substrates for this reaction affording the corresponding
succinimide products in high yields. It is interesting to note
that on reaction of 1c, displaying phenyl groups at both the
α-
and -position with respect to the carbonyl motif, complete
β
selectivity was observed for C(sp3)–H activation at the methyl
groups over traditionally more reactive sp2-hybridised C–H
bonds to form 7c. Although similar selectivities were observed
in a related Ni-catalysed C–H carbonylation reaction,14 this
represents a rare example of competitive aliphatic over
aromatic C–H activation. Spirocyclic quinolinamides comprised
(entries 10-11). Although
a variety of silver salts were
tolerated by the reaction, silver carbonate proved to be the
superior oxidant (see supporting information). A range of
of
a
cyclohexane or substituted piperidine moiety also
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provided synthetically useful yields of the desired succinimide prepared in 55% yield. We found that the Co-catalyzed
products 7f and 7g carbonylation process performed well on a larger, 5 mmol
scale to give an 80% yield of the succinimide product 7a
.
.
Table 2. Reaction scope
Finally, we demonstrated that the succinimide products
were compatible with further derivatisation: reductive ring
opening of 7c with LiAlH4 generated amino-alcohol
yield; hydrolysis of succinmide 7c with
hydrochloric acid led to the formation of substituted succinic
acid in 88% yield, with release of the 8-aminoquinoline
8
in 66%
3
M aqueous
9
directing group; and treatment of 7c with morpholine afforded
the ring-opened bis-amide 10 in 77% yield with complete
regioselectivity.
Scheme 3 Product derivatisations
Conclusions
In summary, we have developed a Co-catalysed carbonylative
cyclisation procedure of unactivated, aliphatic C–H bonds.
Central to the success of this procedure is the stabilising effect
of the quinolinamide directing group. The process tolerates a
range of functionalised substrates to generate substituted
succinimide products. Importantly, the operationally simple
reaction conditions are complemented by the ability utilise an
atmospheric pressure of carbon monoxide. While the
mechanism of this process remains unclear with respect to the
catalytic function of the cobalt salts, an elucidation of the role
of the essential stoichiometric Ag additives will also be
crucial.15 Moreover, to fully realise the full synthetic potential
of C–H activation with earth abundant catalysts, an important
challenge will be to develop processes that do not rely on
precious metal additives and bespoke directing auxiliaries. On
going mechanistic studies should reveal further opportunities
refine these transformations and lead to the development of
new efficient Co-catalyzed C–H activation reactions.
a80% on 5.00 mmol scale. b 20 mol% Co(acac)2 used.
Substrates containing sensitive ester functionalities, as well as
electron-withdrawing trifluoromethyl groups were all
accommodated by the reaction, affording the succinimides in
51-80% yield (7g-2i). Succinimide 7j could also be prepared in
moderate yield by the C–H carbonylation of a protected α-
amino acid derivative. Selective methylene C–H activation onto
a cyclopropyl group provided the bicyclic succinimide products
Acknowledgements
in reasonable yields (7k
– 7n). Interestingly, the butyramide-
We are grateful to the Herchel Smith Foundation for a
scholarship (P.W.) and the Royal Society (Wolfson Merit
Award, M.J.G) and the EPSRC and ERC for Fellowships (M.J.G).
Mass spectrometry data were acquired at the EPSRC UK
National Mass Spectrometry Facility at Swansea University.
derived substrate,10 displaying a partially substituted carbon
atom between the carbonyl group and the site of C–H
activation successfully underwent C–H carbonylation in 66%
yield, to succinimide 7o; this substrate was unreactive under
Ge’s Co-catalysed C–H amidation procedure.9a Alanine derived
7p, containing a protected amine group, was also successfully
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O
N
Co(acac)2 (10 mol%),
O
Ag2CO3 (3 equiv),
N
H
N
PhCO2Na (1.5 equiv),
N
O
H
CO, PhCl, 160 ºC
carboxamide derivative
substituted succinimide
O
N
Co
Xn
N
cobaltacycle
TOC
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