Cobalt-catalyzed C-H olefination of aromatics with unactivated alkenes

Article abstract of DOI:10.1039/c6cc04835h

A cobalt-catalyzed C-H olefination of aromatic and heteroaromatic amides with unactivated alkenes, allyl acetates and allyl alcohols is described. This method offers an efficient route for the synthesis of vinyl and allyl benzamides in a highly stereosele

Full text of DOI:10.1039/c6cc04835h

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Graphical Abstract
DOI: 10.1039/C6CC04835H
Cobalt-Catalyzed C-H Olefination of Aromatics with Unactivated
alkenes
Ramasamy Manoharan, Ganesan Sivakumar and Masilamani Jeganmohan*
Abstract:
A cobalt-catalyzed C-H olefination of aromatic and heteroaromatic amides with unactivated alkenes, allyl acetates and allyl alcohols
is described. This method offers an efficient route for the synthesis of vinyl and allyl benzamides in a highly stereoselective manner.

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DOI: 10.1039/C6CC04835H
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COMMUNICATION
Cobalt-Catalyzed C-H Olefination of Aromatics with Unactivated
Alkenes
Ramasamy Manoharan, Ganesan Sivakumar and Masilamani Jeganmohan*
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
5
DOI: 10.1039/b000000x
report an unprecedented cobalt-catalyzed aminoquinoline directed
50 C-H olefination of aromatics with unactivated alkenes, allyl
acetates and allyl alcohols. The present method provides
synthetically highly useful alkenylated benzamides in a highly
stereoselective manner (eq 3). Interestingly, allyl acetates and
allyl alcohols provided vinylated benzamides without cleavage of
55 OAc or OH groups on the alkene moiety. Meanwhile, unactivated
alkenes afforded allyl benzamides exclusively in a highly
stereoselective manner. It is observed that the ortho substituent
on the benzamide moiety is crucial for the observation of
allylated products in the reaction with unactivated alkenes in a
60 highly regioselective manner.
A
cobalt-catalyzed C-H olefination of aromatic and
heteroaromatic amides with unactivated alkenes, allyl
acetates and allyl alcohols is described. This method offers an
efficient route for the synthesis of vinyl and allyl benzamides
10 in a highly stereoselective manner. It is observed that the
ortho substituent on the benzamide moiety is crucial for the
observation of allylated products in unactivated alkenes.
The C-H bond functionalization of substituted aromatics and
heteroaromatics is a subject of intense interest in modern organic
15 synthesis. Particularly,
a metal-catalyzed chelation-assisted
selective olefination at the inactive C-H bond of substituted
aromatics with alkenes is an efficient method for synthesizing
arylated alkenes in a highly atom- and step-economical manner
from easily available starting materials.1 Traditionally, arylated
20 alkenes are efficiently prepared by a palladium-catalyzed cross-
coupling of organic electrophiles or organometallic reagents with
alkenes in a highly stereoselective manner.2 Alternatively,
arylated alkenes are prepared by a palladium-catalyzed C-H
olefination of electron-rich aromatics with alkenes via an
25 electrophilic metalation pathway.3 However, controlling the
selectivity of this reaction is very difficult and also a large excess
amount of aromatics is required to perform the reaction.
Meanwhile, the C-H olefination of aromatics with alkenes is
achieved selectively in the presence of a metal catalyst via
30 chelation-assisted metalation pathway by taking the advantage of
coordinating ability of heteroatom with a metal. 4 By employing
this pathway, an alkene moiety can be successfully installed at
the ortho as well as meta position of substituted aromatics
selectively.5-7 However, in this type of alkenylation reaction, only
35 conjugated alkenes such as acrylates, vinyl sulfones,
acrylonitriles, acrylamides and styrenes are extensively used (eq
1). The selective C-H olefination with unactivated alkenes are
rare and very challenging to succeed due to the less reactivity of
alkenes and formation of mixtures of linear as well as branched
40 isomers (eq 2).8
Meanwhile, most of this transformation relies on second and
third row noble metals such as palladium, rhodium, ruthenium
and iridium. However, these noble metals are less abundant in
nature and very expensive. Thus, the development of new C-H
45 bond transformation reaction by using more abundant and
sustainable first row transition metal catalysts is highly important.
Very recently, a cobalt complex has been identified as an efficient
catalyst for the C-H bond transformation reaction.9-11 Herein, we
Scheme 1 Scope of unactivated alkenes 2a-k
Treatment of 2-methyl benzamide 1a with 1-decene (2a) (3.0
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.
equiv) in the presence of Co(OAc)2 4H2O (10 mol %), Ag2O (2.2 35 olefinated product 3haa was observed in 36% yield. It is very
equiv) and pivalic acid (30 mol %) in chlorobenzene under air at
100 C for 24 h provided ortho allylated benzamide 3aa in 63%
yield (For detailed optimization studies, please see ESI, Tables
S1-S4). In most of the reported C-H olefination of aromatics with
interesting to note that in products 3fa and 3gh, a typical Heck-
type vinylated product was observed. SurprisingVlyie,w AirnticlebOisnline
DOI: 10.1039/C6CC04835H
olefinated products 3faa, 3ghh and 3haa, vinylation was
observed at one of the ortho carbons and allylation was found in
5
unactivated alkenes, a mixture of linear as well as branched 40 another ortho carbon. This results clearly reveals that a sterically
vinylated products was observed.8 Interestingly, in the present
reaction, only a linear type allylated product was observed in a
highly stereoselective manner.
hindered ortho substituted benzamides including ortho
alkenylated benzamides prefer to give allylated products in a
highly stereoselective manner. Whereas, a less hindered para
substituted benzamides prefer to give a vinyl type coupling
10
The scope of allylation reaction was examined with various
unactivated alkenes (Scheme 1). 1-Hexene (2b), 1-octene (2c) 45 product.
and allylbenzene (2d) reacted efficiently with 1a, providing
allylated aromatics 3ab-ad in good yields. Further, functional
group such as ester, bromo and OH substituted unactivated
Impressed by these results, the olefination reaction was
examined with allyl acetates and alcohols (Table 1 and Scheme
3). Treatment of 4-chlorobenzamide (1g) with allyl acetate (2l)
under the optimized reaction conditions in the presence of 3.0
15 alkenes 2e-h provided products 3ae-ah without affecting the
sensitive groups. In all these alkenes including allylbenzene (2d), 50 equiv of pivalic acid gave ortho vinylated product 4gl in 42%
only linear type allylated product was observed. 3,3-Dimethylbut-
1-ene (2i) reacted with 1a giving vinylated benzamide 3ai in 57%
yield. But, in vinylcyclohexane (2j) and vinylcyclooctane (2k),
20 an approx. 3:1 ratio of allyl and vinyl benzamides 3aj-ak’ were
observed.
yield. It is surprising that in product 4gl, acetate moiety of 2l was
not cleaved and only a Heck-type vinylation product was
observed. In the reported metal-catalyzed C-H bond
functionalization reaction, allylic acetates mostly serve as an
55 allylating agent, providing allylated product.12d In the present
report, a typical Heck type vinylation product was observed in
allyl acetate without cleavage of OAc group. The scope of
olefination reaction was examined with substituted benzamides
having functional groups such as I, Br, and OMe by using allylic
60 acetate (2l) (Table 1). In all these reactions, the expected
vinylated products 4hl-jl were observed in moderate yields
without acetate cleavage (entries 2-5). A heteroaromatic amide 1k
reacted with 2l, affording product 4kl in 30% yield. The
alkenylation reaction of unsymmetrical benzamides 1l-m with 2l
65 was highly site selective, providing vinylated products 4ll-lm in
moderate yields (entries 7 and 8). In benzamides 1l-m,
regioselectively a less hindered C6-H was involved.
Table 1 Vinylation of substituted benzamides with allyl acetatea
Entry
Alkenes 2
Product 3
Yield (%)b
1
2
3
4
5
1g: R1 = Cl
1h: R1 = Br
1i: R1 = I
4gl: R1 = Cl
4hl: R1 = Br
4il: R1 = I
42
37
33
32
29
1f: R1 = Me
1j: R1 = OMe
4fl: R1 = Me
4jl: R1 = OMe
O
6
30
Q
S
N
H
1k
Scheme 2 Scope of substituted benzamides 1b-h
The allylation reaction was further examined with substituted
25 benzamides 1b-h (Scheme 2). ortho Bromo 1b and phenyl 1c
substituted benzamides reacted with unactivated alkenes such as
1-decene (2a) or 9-decen-1-ol (2h) providing the expected
allylated products 3ba-ca in good yields. Sterically hindered 2-
bromo-4,5-dimethoxy benzamide 1d and 1-naphthyl amide 1e
30 also efficiently participated in the reaction affording products 3da
and 3ea in good yields. However, the reaction of para methyl 1f
and chloro 1g substituted benzamides provided a mixture of
mono as well as bis olefinated benzamides 3fa-gh and 3faa-ghh
in moderate yields. In para bromo benzamide 1h, only bis
7
8
1l: R3 = OMe
1m: R3 = I
4ll: R3 = OMe
4ml: R3 = I
33
32
aAll reactions were carried out using 1f-m (100 mg), allyl acetate (2l) (3.0
70 equiv), Co(OAc)2 4H2O (10 mol %), pivalic acid (3.0 equiv), and Ag2O
.
(2.2 equiv) in chlorobenzene (4.0 mL) under air at 100 C for 24 h.
bIsolated yield.
The olefination reaction was further examined with substituted
allyl alcohols and allyl acetates (Scheme 3). Various allyl
2
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alcohols and acetates 2m-r were efficiently involved in the 35 Co(III) species 7 (Scheme 4) 11n. The reaction did not proceed in
reaction with para or meta substituted benzamides 1f or 1l,
yielding the expected vinyl benzamides 4lm-fr in moderate
yields. Particularly, in meta substituted benzamide 1l, vinylation
selectively takes place at the C-6 position. It is observed that if
any coordinating group such as ester is present at the γ-carbon of
alkene, vinyl type product was observed exclusively (Scheme 3).
If there is no coordinating group in γ-carbon, only allyl type
products were observed (Scheme 1).
the absence of either Ag2O or pivalic acid (see ESI for details).
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DOI: 10.1039/C6CC04835H
5
Scheme 4 Proposed mechanism
It is believed that the β-hydride elimination proceeds via a
40 different mechanism in intermediate 9 based on the alkene
coupling partner and substituent on the benzamide moiety. In
allyl acetates and alcohols, intermediate 9a would be formed. The
OAc or OH substituent at the γ-carbon of alkene intramolecularly
coordinates with a cobalt species in intermediate 9a and stabilizes
45 it (eq 6). The syn coplanarity arrangement of metal with Cβ-H is
required for β-hydride elimination. In intermediate 9a, the
rotation of a single bond to obtain syn coplanarity is restricted in
both sides due to the strong coordination of aminoquinoline
ligand as well as OR of alkene into a cobalt metal.12 It is likely
50 that the base AgO- or RO- could deprotonates the benzylic C-H
bond to form vinylated product 4. [7e] In unactivated alkenes, there
is no coordinating group present at the γ-carbon. Thus, to obtain
the coplanarity, a single bond rotation takes place towards alkyl
side easily in intermediate 9b without any restriction (eq 6). After
55 rotation, β-hydride elimination takes place at alkyl side efficiently
and giving allyl benzamides 3. In this case, β-hydride elimination
was not found at the benzylic C-H bond due the strong complex
formation of aminoquinoline ligand into a cobalt species. It is
also further believed that an ortho substituent in benzamide can
60 able to give a more conformational strain in the intermediate 9b.
Thus, the allylic selectivity is better in ortho substituted
benzamides (particularly products 3faa, 3ghh, 3haa and 5a-b). It
is unclear that the observation of vinylated products 3fa and 3gh
in the reaction of para substituted benzamides 1f or 1g with
65 alkenes 2a or 2h.
10
Scheme 3 Scope of allyl alcohols and acetates
A possibility of sequential C-H olefination at the ortho C-H
bond of ortho olefinated benzamides 4 with unactivated alkenes 2
was examined (eq 4). When products 4jl or 4fl was treated with
15 1-octene (2a) or allylbenzene (2d), allyl aromatic alkenes 5a-b
were observed in good yields in a highly regioselective manner.
In this way, unsymmetrical 2,6-diolefinated benzamides can be
prepared selectively in good yields. Surprisingly, product 3ah
underwent double bond migration towards aromatic moiety in the
20 presence of base, affording ortho vinylated aromatic amide 6 in
76% yield (eq 5).
A possible reaction mechanism is proposed to account for the
present reaction in Scheme 4. The catalytic reaction is likely
25 started with a Co(III) species 7 which obtained by the oxidation
of Co(II) species in the presence of Ag+ and pivalic acid. The
coordination of nitrogen atom of amide 1 to a cobalt (III) species
7 followed by acetate-mediated C-H bond activation provides a
cobaltacycle intermediate 8. Coordinative insertion of the double
30 bond of alkene 2 into a C-Co bond of intermediate 8 affords
intermediate 9. β-Hydride elimination of intermediate 9 gives
olefinated product 3 and regenerates the active cobalt(III) species
7 by the reaction of Co(I) with Ag2O and ROH.11m The reaction
of 1f with CD3OD clearly reveals that the reaction starts with a
In conclusion, we have demonstrated a cobalt-catalyzed
C-H olefination of benzamides with unactivated alkenes, allyl
acetates and allyl alcohols. The present protocol allows an
70 efficient route to synthesize vinyl and allyl benzamides in a
highly stereoselective manner. It is observed that the ortho
substituent on the benzamide moiety is crucial for the observation
of allylated products in unactivated alkenes. The mechanistic
investigation suggest that a Co(III) acetate species is involved in
75 the C-H bond activation. A detailed mechanistic investigation and
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the extension of a similar reaction in other organic molecules are
in progress in our laboratory.
70
75
80
85
We thank the DST-SERB (EMR/2014/000978), India for the
support of this research. R. M. and G. S. thank the CSIR for a
fellowship.
DOI: 10.1039/C6CC04835H
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Notes and references
a Department of Chemistry, Indian Institute of Science Education and
Research, Pune 411021, India; E-mail: mjeganmohan@iiserpune.ac.in
† Electronic Supplementary Information (ESI) available: Detailed
9
10 experimental
procedures
and
spectroscopic
data.
See
DOI: 10.1039/b000000x/
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