Rh(iii)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds

Article abstract of DOI:10.1039/c9cc02391g

A straightforward Rh(iii)-catalyzed general strategy was developed for the introduction of naphthol/phenol moieties to the C(sp³)-H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides. The developed method was further extended towards the arylation of 8-formylquinolines to accomplish diarylketone derivatives. The method is simple, relatively rapid, and chemo and regioselective with a wide scope and functional group tolerance. The synthetic utility was established through gram-scale synthesis and biologically active molecule construction.

Full text of DOI:10.1039/c9cc02391g

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DOI: 10.1039/C9CC02391G
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Rh(III)‐Catalyzed straightforward Arylation of 8‐Methyl/
FormylQuinolines using Diazo Compounds
Bidhan Ghosha and Rajarshi Samantaa*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
A
straightforward Rh(III)‐catalyzed general strategy was elegantly explored by Sanford’s10a,b, Daugulis’s10c, Yu’s10d and
developed for the introduction of naphthol/phenol moieties to Larossa’s10e groups with various coupling partners.
the C(sp3)‐H bond of 8‐methylquinoline using diazonaphthalen‐
2(1H)‐ones/quinone diazides. The developed method was further
extended towards the arylation of 8‐formylquinolines to
accomplish diarylketone derivatives. The method is simple,
relatively rapid, chemo and regioselective with a wide scope and
functional group tolerance. The synthetic utility was established
through gram‐scale synthesis and biologically active molecule
construction.
Site‐selective C‐H arylation especially under Rh(III)‐catalyzed
conditions has flourished widely owing to its maximum
efficiency, robustness, and synthetic applicability.1 In this
regard, transition metal catalyzed the introduction of the
naked phenol moiety into the unactivated C‐H bonds is much
less explored. This can be ascribed due to the poor stability of
phenol moiety under the oxidative/harsh reaction conditions
Scheme 1 Transition metal catalyzed arylation using quinone diazides.
In recent progress, Chang’s11a and Glorius’ groups11b,c also
developed rhodium‐catalyzed arylation at this place. However,
none of these methods are suitable to introduce unprotected
phenol/naphthol moieties at the primary C(sp3)‐H bonds.
Incidentally, site‐selective metal–carbene insertion into a
primary C(sp3)–H bond remains a challenging task.12 Inspired
by the recent advancement on directed C‐H metalation, metal‐
carbene generation and subsequent migratory insertion with
diazo compounds13,14, direct quinoline C8‐methyl alkylation
was subjected under Rh(III)‐catalysis by Zhou’s group15 and
under Co(III)‐catalysis by Shi’s group (Scheme 1bii)16. Based on
our ongoing interest in the directed functionalization of C‐H
bonds,17 we hypothesized that diazonaphthalen‐2(1H)‐
one/quinonediazides might be the suitable coupling partner to
introduce naphthol/phenol moieties at the C8‐methyl group of
quinoline scaffolds. Herein, we describe an efficient Rh(III)‐
catalyzed redox‐neutral C(sp3)/ C(sp2)‐H arylation of 8‐
methylquinoline and 8‐formylquinoline using diazonaphthalen‐
2(1H)‐one/quinonediazide (Scheme 1c).
employed.2
Though
underexplored,
recently
quinonediazides/diazonaphthalen‐2(1H)‐ones are recognized
as promising coupling partners for (sp2)C‐H arylations (Scheme
1a).3,4 After the Baran group’s cyclopropanation study with
quinone diazides3a, Li and Wang’s group utilized these
compounds for the introduction of phenol moieties into the
arene C(sp2)‐H bonds under Rh(III) or Ir(III)‐catalysis.3b Further,
Cui4e, Yang4f, Antonchick & Waldmann4g and our group3c,4i used
these diazo compounds for chelation assisted the site‐selective
introduction of unmasked phenol/naphthol moieties into
C(sp2)‐H bonds. However, there is no report on chelation
assisted primary C(sp3)‐H arylation to obtain direct unmasked
phenol/naphthol moieties. Strategically, 8‐methylquinoline
was considered as a model substrate for various C(sp3)‐H bond
functionalizations5 to provide C‐C,6 C‐N,7 C‐O,8 or C‐Si9 bonds
formations especially arylations (Scheme 1b)10,11. Palladium‐
catalyzed arylations at the C8‐methyl group of quinolines were
We embarked our studies by examining the reaction
conditions in the coupling of 8‐methylquinoline (1a) with
diazonaphthalen‐2(1H)‐one (2a) at 80 °C under [Cp*RhCl2]2 (2
mol%), AgSbF6 (8 mol%) and pivalic acid (20 mol%) catalyzed
conditions.
a. Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur
721302, India.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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Table 1 Optimization of primary C(sp3)‐H arylation of 8‐methylquinolinea
obtained in the presence of strong electron withdrawing ‐NO2
group (Scheme 2, 3n).
View Article Online
DOI: 10.1039/C9CC02391G
entry
1
2
3
4
5
6
7
8
solvent
toluene
MeCN
dioxane
TFE
additive 1
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgSbF6
AgNTf2
AgPF6
additive 2
PivOH
PivOH
PivOH
PivOH
PivOH
PivOH
AcOH
AdCO2H
PivOH
PivOH
PivOH
PivOH
PivOH
PivOH
PivOH
PivOH
PivOH
PivOH
‐
yield (%)b
39
45
51
62
71
96
78
62
55
63
72
59
Trace
Trace
68
75
nd
tAmOH
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
9
10
11
12
13
14
15c
16d
17e
18
19
AgBF4
AgOTf
AgNO3
AgOAc
AgSbF6
AgSbF6
AgSbF6
‐
Scheme 2 Scope of (sp3)C‐H arylation of 8‐methylquinolines with diazonaphthalen‐
2(1H)‐ones/quinonediazides. Reaction conditions: 1 (0.1 mmol), 2a (0.12 mmol),
[Cp*RhCl2]2 (2 mol%), AgSbF6 (8 mol%), pivalic acid (20 mol%), DCE (0.1 M), air, 80 °C, 2
h. aReaction was done in 5 mmol scales with 1 mol% [Cp*RhCl2]2.
nd
nd
DCE
AgSbF6
aReaction conditions: 1a (0.1 mmol), 2a (0.12 mmol), [Cp*RhCl2]2 (2 mol%),
AgSbF6 (8 mol%), Ag salt (8 mol%), carboxylic acid (20 mol%), solvent (0.1 M), air,
2 h, 80 °C.bIsolated yields. creaction time: 6 h, 60 °C. d[Cp*RhCl2]2 (1 mol%), 80 °C,
6 h. ewithout [Cp*RhCl2]2 catalyst.
Gratifyingly,
more
π‐conjugated
5‐aryl/heteroaryl‐8‐
methylquinoline furnished satisfying yields of corresponding
products (Scheme 2, 3o and 3p). Further, aromatic ring fused
10‐methylbenzo[g]quinoline was transformed into its
corresponding product in very good yield (Scheme 2, 3q). To
demonstrate the scalability of this method, 1a and 2a were
coupled to obtain the desired product 3a in gram scale under
reduced catalyst loading (1 mol%) with satisfying 71% isolated
yield (Scheme 2, 3a).
To our delight, an exclusively C(sp3)–H β‐naphthol coupled
compound (3a) had formed with a moderate yield (Table‐1,
entry‐1). For further optimization, several common solvents
were screened (Table 1, entries 2‐5), DCE was found to be the
best (Table 1, entry 6) with 96% isolated yield of desired
product 3a. No improvement of desired product’s yield was
observed varying less or bulkier carboxylic acids as an additive
(Table 1, 7‐8). For more accretion in the yield of 3a, different
silver salts were tested, but no additional improvement was
realized (Table 1, entries 9‐14). Lowering the reaction
temperature to 60 °C diminished the yield of the desired
product to 68% (Table 1, entry 15). Decreasing the catalyst
loading led to an inferior yield of 3a, even at a higher
temperature (Table 1, entry 16). Incidentally, other cheaper
transition metal catalysts like [Cp*IrCl2]2, [Cp*CoI2]2, RhCl3 did
not turn to be an effective catalyst. Importantly, there was no
desired product formation in the absence of any of these
Rh(III) catalyst, AgSbF6 or pivalic acid (Table 1, entries 17‐19).
After the establishment of the optimized conditions, a
thorough assessment of the substrate scope for 8‐
methylquinolines was executed (Scheme 2). Different halogen
substitutions at the various position of quinoline moiety were
Next, various literature known diazanaphthalenes‐2(1H)‐
ones18 were introduced to examine the efficacy of the
developed protocol. Halogen, electron‐donating and electron‐
withdrawing
containing
diazanaphthalenes‐2(1H)‐ones
afforded the desired products in excellent yields (Scheme 2,
4a‐4d). Moreover, more conjugated phenyl ring containing
diazonaphthalen‐2(1H)‐one led to its corresponding product
with commendable yield (Scheme 2, 4e). We were pleased to
observe that 2‐diazanaphthalenes‐1(2H)‐one and 4‐
diazonaphthalen‐1(4H)‐one derivatives provided desired
products under optimized conditions (Scheme 2, 4f‐4g).
Notably, p‐quinonediazides provided the desired products
under optimized conditions albeit in poor yields (Scheme 2,
4h‐4i). In many cases, the reduced stability of the p‐quinone
diazides restricted to its limited scope. Benzophenones are
well‐admired scaffolds to the synthetic and medicinal chemists
owing to its presence in many bioactive compounds. However,
there are limited approaches to construct this scaffold directly
from its aldehyde‐congener via the chelation assistance.19
Strategically, the Rh(III)‐catalyzed optimized conditions was
further extended to the direct synthesis of benzophenone
derivatives from quinoline‐8‐carbaldehydes (Scheme 3).
safely tolerated with excellent yields (Scheme 2, 3b‐3g).
Electron donating methoxy and a methyl group at the C6
position was firmly accommodated (Scheme 2, 3h‐3i). Other
alkyls, cyclopropyl and vinyl group at the C5‐position worked
uninterruptedly with impressive yields (Scheme 2, 3j‐3m).
Importantly, an impressive yield of the desired product was
2 | J. Name., 2012, 00, 1‐3
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Pleasingly, the reaction proceeded much faster to provide the pathway of this coupling reaction is proposed V(ieSwcAhreticmleeOn6lin)e.
desired products in excellent yields. Quinoline‐8‐ Initially, a cationic Rh(III)‐species was forDmOeI:d10v.i1a03li9g/aCn9CdCs0w23it9c1hG.
carbaldehydes having halogen groups at the different positions Next, the cationic Rh(III)‐species coordinates to the N atom of
were found to be active substrates under the optimized 8‐methylquinoline (1a) to form five‐membered rhodacycle
conditions (Scheme 3, 6b−6g). Both, electron donating and via the carboxylate assisted rate‐determining C8‐methyl
withdrawing group were well accommodated (Scheme 3, 6h
(sp3)C‐H activation. Subsequently, the diazonaphthalen‐2(1H)‐
6i). Further, different diazanaphthalenes‐2(1H)‐one derivative one (2a) reacts with intermediate species to generate metal‐
A
‐
A
with halogen, electron‐donating, withdrawing and phenyl ring carbenoid intermediate
could also be tolerated under the reaction protocol with
satisfying yields (Scheme 3, 6j‐6n). Moreover, 2‐
diazanaphthalenes‐1(2H)‐one also worked well to afford α‐
naphthol derivative (Scheme 3, 6o).
B.
Scheme 4 Product modifications and applications
Scheme 5 Kinetic studies and control experiments.
Scheme 3 Scope of 8‐formylquinoline arylation: Reaction conditions.5 (0.1 mmol), 2
(0.12 mmol), [Cp*RhCl2]2 (2 mol%), AgSbF6 (8 mol%), pivalic acid (20 mol%), DCE (0.1
M), air, 80 °C, 1h.
[Cp*RhCl2
]
2
3a or 6a
PivOH/AgSbF6
1a or 5a
protonation &
rearomatization
C-H bond
Cp*Rh(III) active
H+
metalation
species
H+
+
]
+
]
N
Finally, the structure was unequivocally established by a single
x‐ray crystal analysis of compound 6j (CCDC no: 1899501). For
the synthetic expediency, we performed the selective
reduction of 3a using catalytic NiCl2∙6H2O and NaBH4 to furnish
O
RhIII Cp*
O
N
N
RhIII
A
O
RhV
O
migratory
insertion
Cp*
Cp*
C
2a
metal carbenoid
formation
O
N2
B
the tetrahydroquinoline derivative
Next, the developed method was strategically applied to
synthesize cannabinoid CB1 receptor ligand20
via the
7 in 62% yield (Scheme 4a).
Scheme 6 Plausible mechanism.
9
Next, the migratory insertion provides intermediate
the protodemetalation followed by rearomatization of
affords the desired 8‐methylquinolino β‐naphthol adduct (3a
with the regeneration of active Rh(III) catalyst. Presumably,
the similar catalytic cycle is occurring for 8‐formylquinoline
derivative via the initial C(sp2)‐H metalation.
In conclusion, we have developed the Rh(III)‐catalyzed
introduction of phenol/naphthol moieties at the primary
C(sp3)‐H bond of 8‐methyl quinoline derivatives using
quinonediazides/diazonaphthalen‐2(1H)‐ones. The method
was further explored for the direct arylation at the C8‐formyl
quinolines to generate benzophenone type scaffolds. The
practical applicability was realized with gram scale synthesis
and biologically important compounds through post
modifications.
C. Finally,
formation of 6p and its subsequent alkylation (Scheme 4b).
To shed light on mechanistic insight, we carried out several
control experiments. First, H/D scrambling of 1a was observed
under CD3CO2D‐CD3OD conditions. This result indicates that
(sp3)C−H bond metalaꢀon is reversible here in the absence of
coupling partner 2a (Scheme 5i). However, in the presence of
2a, no deuteration was detected in the re‐isolated 1a and the
product 3a, indicating that the further steps were much faster
C
)
than the competitive deuteration (Scheme 5ii). In
a
competition between 6‐methoxy and 6‐nitro‐dertivatives (1h
and 1n), the coupling favored the electron‐rich quinoline in a
~5:1 ratio (Scheme 5iii). Next, a kinetic isotope effect (KIE) was
measured for this C–H activation process (Scheme 5iv). Parallel
competition experiments furnished steady outcomes with a
large magnitude of KIE ~6.8 suggesting that the C–H bond
cleavage was a turnover‐limiting step in the catalytic cycle (see
the Supporting Information). Based on the above experiments
Financial support by the SERB, India (CRG/2018/000630) and
CSIR, India (02(0323)/17/EMR‐II) are thankfully acknowledged.
BG thanks CSIR for his fellowship.
and precedent literature3,4,15,16
, a plausible mechanistic
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1‐3 | 3
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6, 5930; (f) G. S.
X.‐F. Yang, T.‐P. Loh, ACS Catal., 2016,
Conflicts of interest
There are no conflicts to declare.
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