Cobalt-catalyzed chelation assisted C-H allylation of aromatic amides with unactivated olefins

Article abstract of DOI:10.1039/c6cc05330k

The cobalt-catalyzed chelation assisted ortho C-H allylation of aromatic amides with unactivated aliphatic alkenes is reported. The reaction proceeds in air under mild reaction conditions, providing allylated products in good to excellent yields with high E-selectivities. This operationally simple method shows a high functional group tolerance.

Full text of DOI:10.1039/c6cc05330k

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DOI: 10.1039/C6CC05330K
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Cobalt‐Catalyzed Chelation Assisted C‐H Allylation of Aromatic
Amides with Unactivated Olefins†
Takuma Yamaguchi,‡ Yadagiri Kommagalla,‡ Yoshinori Aihara, and Naoto Chatani*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Abstract: The cobalt‐catalyzed chelation assisted ortho C‐H C‐H functionalizations.10 Herein, we report on the first Co‐
allylation of aromatic amides with unactivated aliphatic alkenes is catalyzed allylic type C‐H bond functionalization with
reported. The reaction proceeds under air under mild reaction unactivated alkenes (eq 3, Scheme 1).
conditions, providing allylated products in good to excellent yields
with high E‐selectivities. This operationally simple method shows
a high functional group tolerance.
Transition‐metal‐catalyzed specific C‐C bond formation
from ubiquitous C‐H bonds is a challenging and attractive
method for the synthesis of complex organic molecules, some
of which are critical components of pharmaceuticals and
functional
materials.1‐3
Direct
allylation
via
C‐H
functionalization is a highly important method and a long
standing challenge from the standpoint of its synthetic utility,
atom and step economy.4,5 Numerous examples of allylation
reaction have been reported, but all involve the use of
activated or prefunctionalized coupling partners, such as allyl
halides and phosphates (eq 1, Scheme 1).6 Compared with the
extensively studied oxidative alkenylation of C‐H bonds with
styrenes and acrylates, unactivated olefins have not been
extensively employed in alkenylation reactions, due to
concerns regarding their poor reactivity and selectivity.7 In
regard to catalysts, in C‐H functionalization with second and
third row transition metals, such as Pd, Rh, Ru and Ir a myriad
number of examples can be found in the literature,1,8 but the
use of early and earth abundant transition metals in C‐H
functionalization reactions is still limited. Chemists shifted
their focus towards the development of C‐H functionalization
with inexpensive and earth abundant first row transition
metals, such as Co and Ni.9 It is known that the Co‐catalysts
are stable in air, inexpensive and have the potential for novel
Scheme 1 Reaction of C‐H bonds with olefins
The quest for selective allylation with unactivated terminal
olefins started with aromatic amides that contain an 8‐
aminoquinoline directing group, which is unexceptionally
promising tool for use in C‐H functionalizations.11 The reaction
started by treating 1a with 1‐octene (2a) in the presence of
Co(OAc)2.4H2O (20 mol%) as a catalyst and Ag2CO3 (1
equivalent) as an oxidant, in dichloroethane (DCE) at 120 °C for
24 h (entry 1, Table 1). Interestingly, the allylated product 3aa
was produced in the form of a mixture of E/Z isomers in good
yield (77%) with the E‐isomer being favored. It was gratifying
to learn that the allylated product was produced in the
presence of air instead of Heck type vinylated or branched
alkenylated product (eq 2 in Scheme 1).7 However, some
amount of starting material (86% conversion of 1a) remained
after the reaction. This interesting result prompted us to
further investigate suitable conditions for achieving an
improved yield. Optimization studies were started by
surveying a series of potential solvents, including toluene, DMF
and PhCF3. In toluene, good yield were obtained, along with
other unidentified byproducts (entry 2, Table 1). The yield
decreased in the case of PhCF3 and DMF was found to be
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita,
Osaka 565‐0871, Japan. E‐mail: chatani@chem.eng.osaka‐u.ac.jp
‡ The authors contributed equally.
† Electronic Supplementary Information (ESI) available: Experimental details and
Spectroscopic data. See DOI: 10.1039/x0xx00000x
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o
d
e
The reaction was carried at 150 C. Oxidant (0.3 mmol) was used.
ineffective (entries 3 and 4, Table 1). In order to improve the
yield of 3aa and completely convert 1a, the concentrations of
reactants and catalyst loading were examined in separate
experiments. Yields were decreased when the reactants were
diluted and varying the amount of catalyst loading had a
negligible effect on the reaction (see the SI). The use of 2
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DOI: 10.1039/C6CC05330K
The reaction was carried oud for 12 h. f The reaction was carried at 100
oC for 12 h.
With these optimization conditions in hand, we next
evaluated the scope of the reaction with respect to the alkene
being used. Several other unactivated terminal alkenes were
explored in order to expand the scope of the reaction (Table 2).
Some olefins, such as 1‐hexene (2b), allylbenzene (2c) and
allylcyclohexane (2d) were examined, and all were observed to
equivalents of Ag2CO3, however, resulted in
a 100%
consumption of starting material, but product yield was
lowered to 63% (entry 5, Table 1). Several silver salts, including
AgOAc, AgOBz, AgOTf, AgF and AgNO3 were screened (entries
6‐10, Table 1) instead of Ag2CO3, among the screened salts,
AgOAc was found to be effective and 3aa was obtained in 62%
yield with a 64% conversion of 1a. Other silver salts had no
effect. However, none of these modifications had a dramatic
react well with 3ab, 3ac and 3ad being produced in excellent
yields, 76%, 85% and 72% isolated yields, respectively. We
next focused on the functionalized terminal olefins to evaluate
the feasibility of the reaction. The reaction of 1a with 5‐hexen‐
1‐ol (2e), 5‐hexenyl acetate (2f) and methyl ‐5‐hexenoate (2g
gave 3ae 3af and 3ag in 65%, 85% and 65% yields, respectively,
indicating that the reaction tolerated different types of
functional groups. Our attention then focused on the sterically
demanding branched alkenes, 2h and 2i. The reaction of 1a
with 3‐methylhexene (2h) gave the products in a total yield of
)
effect on the yield in the reaction or on the conversion of 1a
.
,
Other cobalt catalysts, including CoBr2 and Co(acac)2 were also
examined, but were not effective (entries 11 and 12, Table 1).
Next, the reaction was conducted at different temperatures,
o
o
100 C, 80 C and room temperature (see the SI). No reaction
was observed when the reaction was run at rt and 3aa was
produced in low yield at 80 °C. When the reaction was carried
out at 100 °C, 3aa was produced in 69% yield with a 73%
conversion of 1a. Gratifyingly, 2 equivalents of Ag2CO3 at
100 °C for 12 h gave 3aa in 83% yield with a 94% conversion of
1a (entry 14, Table1). The reaction was found to be clean with
55% with a 2.8:1 ratio of a mixture of 3ah (E/Z=3.4:1) and 3ah’
.
The reaction with vinylcyclohexane (2i) produced a total yield
of 69% with a mixture of 3ai and 3ai’ in the ratio of 3.2:1. In
both cases, allylated products were the major isomer. 1,6‐
Heptadiene (2j) also reacted efficiently with 1a to provide a
mixture of mono‐ and di‐coupled products, 3aj and 3aj’ in 62%
(E/Z=23:1) and 6% yields, respectively.
1
no other detectable byproducts shown on TLC and crude H
NMR.
Table 2 Alkene scopea, b
Table 1 Optimization of reaction conditionsa
O
Co(OAc)2.4H2O
Ag2CO3
O
O
N
H
R
N
+
N
H
DCE, 100 oC
N
12 h, under air
3
1a
2
R
Q
O
O
Q
Q
N
H
N
N
H
H
2
3ab 76%
3ac 85%
3ad 72%c
(E/Z = 21:1)
(E/Z = 29:1)
O
O
O
Q
N
Q
N
Q
N
H
H
H
OH
OAc
OMe
2
2
2
O
3ae 65%c
3af 85%
3ag 65%c
(E/Z = 25:1)
O
O
O
Q
N
Q
N
Q
N
H
H
H
3ai + 3ai'
(E/Z=3.4:1)
O
3ah
+
3ah' 55% (2.8:1d)
69% (3.2:1d)
O
O
O
Q
Q
N
Q
Q
a
N
H
N
N
H
All reactions involved treating 1a (0.15 mmol), 2a (0.3 mmol) in a
H
H
solvent (0.5 mL) in the presence of the cobalt catalyst (0.03 mmol) and
oxidant (0.15 mmol) for 24 h otherwise stated.
determined by H NMR analysis of the crude reaction mixture using
1,1,2,2‐tetrachloroethane as an internal standard. Values given in the
parentheses are yields of isolated product and starting material (1a). c
2
b
Yields were
3aj 62%
(E/Z=23:1)
3aj' 6%
1
2 | J. Name., 2012, 00, 1‐3
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a
a All reactions involved treating 1a (0.15 mmol), alkene 2 (0.3 mmol) in the
All reactions involved treating
1
(0.15 mmol), 2a (0.3 mmol) in the
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presence of Co(OAc)2.4H2O (0.03 mmol) and Ag2CO3 (0.3 mmol) in DCE for presence of Co(OAc)2.4H2O (0.03 mmol) and Ag2CO3 (0.3 mmol) in DCE
DOI: 10.1039/C6CC05330K
12 h, unless otherwise stated. b The cited yields are for isolated products.
(0.5 mL) for 12 h. The cited yields are for isolated products. The
C
b
C
E/Z ratio was not calculated due to the overlapping of the NMR peaks. d Only reaction was carried out at 120 oC. d 27% of starting material (1c) was
the E‐isomer was obtained.
recovered.
A
deuterium labeling experiment with amide 1a‐d7 with 1‐
Table 3 summarizes the generality of the allylation reaction with
substituted benzamides (1b‐1n). The reaction of o‐phenyl, o‐fluoro,
o‐bromo and o‐trifluoromethyl‐substituted benzamides with 1‐
octene (2a) under optimized reaction conditions provided the
expected allylated products. Next, ortho‐methyl‐substituted
benzamides with other functional groups were examined in order
to check the functional group tolerance of the reaction. An
benzamide substituted with an electron‐donating group, such as
2,3‐dimethyl (1f), 2‐methyl‐3‐methoxy (1g), 2‐methyl‐3‐acetoxy
(1h) reacted efficiently to give 3fa, 3ga and 3ha in 73%, 72% and
65% yields, respectively. Amides with an electron‐withdrawing
substituent, such as 2‐methyl‐3‐fluoro (1i) and trifluoromethyl
benzamide (1j) also reacted with 2a to afford 3ia and 3ja. As shown
in the reaction of 2,5‐dimethyl (1l), 2‐methyl‐5‐fluoro (1m), and 2‐
methyl‐5‐bromo‐substituted benzamides (1n), the reaction was not
sensitive to steric hindrance. The reaction shows a high functional
group compatibility.
octene (2a) indicated that no H/D exchange was detected in
the recovered 1a‐d7. This result indicates that the C‐H bond
cleavage step is irreversible.10a,10d
Scheme 2 Deuterium labeling experiment
Scheme 3 shows a plausible mechanism for the present
allylation reaction. The mechanism is proposed based on our
observations and previous literature reports.10 In the first step,
Ag+ oxidizes Co(II) to a Co(III) species,10d which is critical for the
present reaction to proceed. The coordination of
Co(III) species gives , the acetate mediated abstraction of the
ortho proton leads to the generation of the 5‐membered
cobaltacycle . The insertion of the double bond of the alkene
) into C‐Co bond in provides the 7‐membered cobaltacycle
. The subsequent β‐hydride elimination and oxidation by Ag+
with the
1 to the
A
Table 3 Benzamide scope a, b
B
(
C
2
B
leads to the production of the allylated product
3
regeneration of the active Co(III) species. Based on product
formation, it is assumed that β‐hydride elimination with Ha
leading to the formation of vinylated products is not possible,
due to the rigid 7‐membered metallocycle which is formed by
the strong coordination of the 8‐aminoquinoline group.
Alternatively, a single bond rotation leads to a syn coplanar C‐
Co and C‐Hb allows β‐hydride elimination to form the allylated
products 3.
Co(II)X2
Ag+
O
Ag0
O
NHQ
+ Ag0
N
R
H
Co(III)X3
N
3
Ag+
1
(X = OAc, CO3)
HX
O
O
H
N
N
N
Co
X
Co
N
Ha
R
X
X
Hb
R
C
A
O
N
HX
Co
X
N
2
B
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Scheme 3 Plausible mechanism
Gelman and L. Ackermann, Synlett, 2015, 26, 1596‐1600; (g) S. Bae, H.‐L.
Jang, H. Jung and J. M. Joo, J. Org. Chem., 2015, 80,V6ie9w0‐A6rt9ic7le; O(hn)linYe.
DOI: 10.1039/C6CC05330K
Suzuki, B. Sun, K. Sakata, T. Yoshino, S. Matsunaga and M. Kanai, Angew.
Chem. Int. Ed., 2015, 54, 9944‐9947; (i) D.‐G. Yu, T. Gensch, F. de
Azambuja, S. Vasquez‐Cespedes and F. Glorius, J. Am. Chem. Soc., 2014,
136, 17722‐17725; (j) X. Cong, Y. Li, Y. Wei and X. Zeng, Org. Lett., 2014,
16, 3926‐3929; (k) S. Asako, L. Ilies and E. Nakamura, J. Am. Chem. Soc.,
2013, 135, 17755‐17757; (l) H. Wang, N. Schroeder and F. Glorius,
Angew. Chem. Int. Ed., 2013, 52, 5386‐5389; (m) Y. Aihara and N.
Chatani, J. Am. Chem. Soc., 2013, 135, 5308‐5311; (n) Y. Makida, H.
Ohmiya and M. Sawamura, Angew. Chem. Int. Ed., 2012, 51, 4122‐4127;
(o) S. Fan, F. Chen and X. Zhang, Angew. Chem. Int. Ed., 2011, 50, 5918‐
5923.
In summary, we report herein the Co(OAc)2.4H2O catalyzes
E‐selective allylation reactions with unactivated olefins on
ortho C‐H bonds of benzamides. The reaction proceeds in the
presence of air under mild reaction conditions. It allows an
efficient route to allylation with unactivated alkenes, also has a
wide functional group tolerance. Detailed mechanistic studies
are currently underway in our laboratory.
This work was supported, in part, by a Grant‐in‐Aid for
Scientific Research on Innovative Areas "Molecular Activation
Directed toward Straightforward Synthesis (22105001)" from
Monbusho (The Ministry of Education, Culture, Sports, Science
and Technology), and by JST Strategic Basic Research Programs
“Advanced Catalytic Transformation Program for Carbon
Utilization (ACT‐C) (52571)” from Japan Science and
Technology Agency. Y.A. expresses his special thanks for a JSPS
Research Fellowship for Young Scientists.
7. For unactivated olefins: (a) X. Xue, J. B. Xu, L. J. Zhang, C. H. Xu, Y. X. Pan,
L. J. Xu, H. R. Li and W. D. Zhang, Adv. Synth. Catal., 2016, 358, 573‐583;
(b) Y. Takahama, Y. Shibata and K. Tanaka, Chem. Eur. J., 2015, 21, 9053‐
9056; (c) A. Deb, S. Bag, R. Kancherla and D. Maiti, J. Am. Chem. Soc.,
2014, 136, 13602‐13605; (d) A. S. Tsai, M. Brasse, R. G. Bergman and J. A.
Ellman, Org. Lett., 2011, 13, 540‐542.
8. For selected reviews, see: (a) R. Manikandan and M. Jeganmohan, Org.
Biomol. Chem., 2015, 13, 10420‐10436; (b) C. Cheng and J. F. Hartwig,
Chem. Rev., 2015, 115, 8946‐8975; (c) P. Gao, W. Guo, J. Xue, Y. Zhao, Y.
Yuan, Y. Xia and Z. Shi, J. Am. Chem. Soc., 2015, 137, 12231‐12240; (d) K.
M. Engle, T.‐S. Mei, M. Wasa and J.‐Q. Yu, Acc. Chem. Res., 2012, 45,
788‐802; (e) P. B. Arockiam, C. Bruneau and P. H. Dixneuf, Chem. Rev.,
2012, 112, 5879‐5918; (f) T. Satoh, M. Miura, Chem. Eur. J., 2010, 16,
11212‐11222; (g) T. W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110,
1147‐1169;
9. For reviews of Co and Ni: (a) N. Chatani, Top. Organomet. Chem., 2016,
56, 19‐46; (b) J. Miao and H. Ge, Eur. J. Org. Chem., 2015, 36, 7859‐
7868; (c) B. Su, Z.‐C. Cao and Z.‐J. Shi, Acc. Chem. Res., 2015, 48, 886‐
896; (d) L. C. M. Castro and N. Chatani, Chem. Lett., 2015, 44, 410‐421;
(e) K. Gao and N. Yoshikai, Acc. Chem. Res., 2014, 47, 1208‐1219.
10. (a) M. Moselage, J. Li and L. Ackermann, ACS Catal., 2016, 6, 498‐525;
(b) D. Zell, Q. Bu, M. Feldt, and L. Ackermann, Angew. Chem. Int. Ed.
2016, 55, 7408 –7412; (c) D. Wei, X. Zhu, J.‐L. Niu and M.‐P. Song,
Chemcatchem, 2016, 8, 1242‐1263; (d) P. Gandeepan, P. Rajamalli and
C.‐H. Cheng, Angew. Chem. Int. Ed., 2016, 55, 4308‐4311; (e) V. G.
Landge, G. Jaiswal and E. Balaraman, Org. Lett., 2016, 18, 812‐815; (f) N.
Barsu, M. A. Rahman, M. Sen, and B. Sundararaju, Chem. Eur. J., 2016,
22, 9135 – 9138; (g) M. Sen, B. Emayavaramban, N. Barsu, J. R.
Premkumar, and B. Sundararaju, ACS Catal,. 2016, 6, 2792−2796; (h) J.
Zhang, H. Chen, C. Lin, Z. Liu, C. Wang and Y. Zhang, J. Am. Chem. Soc.,
2015, 137, 12990‐12996; (i) X.‐K. Guo, L.‐B. Zhang, D. Wei and J.‐L. Niu,
Chem. Sci., 2015, 6, 7059‐7071; (j) Grigorjeva and O. Daugulis, Angew.
Chem. Int. Ed. 2014, 53, 10209‐10212; (k) L. Grigorjeva and O. Daugulis,
Org. Lett., 2014, 16, 4684‐4687.
Notes and references
1. For selected reviews, see: (a) T. Gensch, M. N. Hopkinson, F. Glorius and
J. Wencel‐Delord, Chem. Soc. Rev., 2016, 45, 2900‐2936; (b) G. E. M.
Crisenza and J. F. Bower、Chem. Lett., 2016, 45, 2‐9; (c) C. Liu, J. Yuan,
M. Gao, S. Tang, W. Li, R. Shi and A. Lei, Chem. Rev., 2015, 115, 12138‐
12204; (d) P. Gandeepan and C.‐H. Cheng, Chem. Asian J., 2015, 10, 824‐
838; (e) T. Iwai and M. Sawamura, ACS Catal., 2015, 5, 5031‐5040; (f) L.
Yang and H. Huang, Chem. Rev., 2015, 115, 3468‐3517; (g) A. F. M.
Noisier and M. A. Brimble, Chem. Rev., 2014, 114, 8775‐8806; (h). X.‐S.
Zhang, K. Chen and Z.‐J. Shi, Chem. Sci., 2014, 5, 2146‐2159.
2. (a) T. Cernak, K. D. Dykstra, S. Tyagarajan, P. Vachal and S. W. Krska,
Chem. Soc. Rev., 2016, 45, 546‐576; (b) Y. Qiu and S. Gao, Nat. Prod.
Rep., 2016, 33, 562‐581; (c) M. Seki, Org. Process Res. Dev., 2016, 20,
867‐877; (d) L. Ackermann, Org. Process Res. Dev., 2015, 19, 260‐269;
(e) J. He, L. G. Hamann, H. M. L. Davies and R. E. J. Beckwith, Nat.
Commun., 2015, 6, 5943‐5951; (f) J. Yamaguchi, A. D. Yamaguchi and K.
Itami, Angew. Chem., Int. Ed., 2012, 51, 8960‐9009;
3. (a) Y. Kuninobu and S. Sueki, Synthesis, 2015, 47, 3823‐3845; (b) L. G.
Mercier and M. Leclerc, Acc. Chem. Res., 2013, 46, 1597‐1605; (c) J.
Wencel‐Delord and F. Glorius, Nat. Chem., 2013, 5, 369‐375;
4. For the synthetic importance of allyl functional groups, see: a)
Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H.
Yamamoto), Springer, New York, 1999; b) Supplement A: The Chemistry
of Double Bonded Functional Groups, Vols. 1 and 2 (Ed.: S. Patai): The
Chemistry of Functional Groups Series, Parts 1 and 2, Wiley, New York,
1997; c) Comprehensive Organic Functional Group Transformations
(Eds.: A. R. Katritzky, O. Meth‐Cohn, C. W. Rees), Elsevier Science, New
York, 1995.
11. (a) O. Daugulis, J. Roane and L. D. Tran, Acc. Chem. Res., 2015, 48, 1053‐
1064; (b) M. R. Yadav, R. K. Rit, M. Shankar and A. K. Sahoo, Asian J. Org.
Chem., 2015, 4, 846‐864; (c) W. Ma and L. Ackermann, ACS Catal., 2015,
5, 2822‐2825; (d) L. Grigorjeva and O. Daugulis, Org. Lett., 2015, 17,
1204‐1207; (e) X. Wu, K. Yang, Y. Zhao, H. Sun, G. Li and H. Ge, Nat.
Commun., 2015, 6, 6462; (f) G. Rouquet and N. Chatani, Angew. Chem.
Int. Ed., 2013, 52, 11726‐11743
5. While our manuscript was in preparation, the Rh‐catalyzed C‐H
allylation was reported Y. Takahama, Y. Shibata, K. Tanaka, Org. Lett.,
2016, 18, 2934‐2937.
6. (a) G. Cera, T. Haven and L. Ackermann, Angew. Chem. Int. Ed., 2016, 55,
1484‐1488; (b) H. Jo, S. Han, J. Park, M. Choi, S. H. Han, T. Jeong, S.‐Y.
Lee, J. H. Kwak, Y. H. Jung and I. S. Kim, Tetrahedron, 2016, 72, 571‐578;
(c) S. Sharma, S. H. Han, Y. Oh, N. K. Mishra, S. Han, J. H. Kwak, S.‐Y. Lee,
Y. H. Jung and I. S. Kim, J. Org. Chem., 2016, 81, 2243‐2251; (d) Y. Aihara,
J. Wuelbern and N. Chatani, Bull. Chem. Soc. Jpn., 2015, 88, 438‐446; (e)
T. Gensch, S. Vasquez‐Cespedes, D.‐G. Yu and F. Glorius, Org. Lett., 2015,
17, 3714‐3717; (f) M. Moselage, N. Sauermann, J. Koeller, W. Liu, D.
4 | J. Name., 2012, 00, 1‐3
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