10.1002/chem.201805926
Chemistry - A European Journal
COMMUNICATION
[6]
(a) C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 7826. (b) H.
Ochiai, M. Jang, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2008, 10,
2681. (c) K. Kobayashi, Y. Kondo, Org. Lett. 2009, 11, 2035.
(a) F. Effenberger, W. Spiegler, Chem. Ber. 1985, 118, 3900. (b) T.
Hattori, Y. Suzuki, S. Miyano, Chem. Lett. 2003, 32, 454. (c) M.
Yonemoto-Kobayashi, K. Inamoto, Y. Tanaka, Y. Kondo, Org. Biomol.
Chem. 2013, 11, 3773. (d) T. V. Q. Nguyen, J. A. Rodríguez-Santamaría,
W.-J. Yoo, S. Kobayashi, Green Chem. 2017, 19, 2501. (e) T. Mita, H.
Tanaka, K. Michigami, Y. Sato, Synlett 2014, 25, 1291. (f) H. Yoshida, H.
Fukushima, J. Ohshita, A. Kunai, J. Am. Chem. Soc. 2006, 128, 11040.
A. Ueno, M. Takimoto, W. W. N. O, M. Nishiura, T. Ikariya, Z. Hou, Chem.
Asian J. 2015, 10, 1010.
[20] Heteroaromatic substrates bearing phenol-OH or aniline-NH2 moieties as
a directing group were also reported to react with CO2 in the presence of
t-butoxide bases (KO-t-Bu or NaO-t-Bu) to form lactones and lactams,
respectively. (a) Z. Zhang, T. Ju, M. Miao, J.-L. Han, Y.-H. Zhang, X.-Y.
Zhu, J.-H. Ye, D.-G. Yu, Y.-G. Zhi, Org. Lett. 2017, 19, 396. (b) Z. Zhang,
L.-L. Liao, S.-S. Yan, L. Wang, Y.-Q. He, J.-H. Ye, J. Li, Y.-G. Zhi, D.- G.
Yu, Angew. Chem. Int. Ed. 2016, 55, 7068. (c) Z. Zhang, T. Ju, J.-H. Ye,
D.-G. Yu, Synlett 2017, 28, 741.
[7]
[21] Previously reported Brønsted-base-mediated carboxylations of
benzothiophene and benzofuran required strong Brønsted bases such
[8]
[9]
as n-BuLi or LDA, which included a two-step protocol involving
deprotonation and coupling with CO2. For examples, see: (a) D. Matecka,
D. Lewis, R. B. Rothman, C. M. Dersch, F. H. E. Wojnicki, J. R. Glowa,
A. C. DeVries, A. Pert, K. C. Rice. J. Med. Chem. 1997, 40, 705. (b) B.
Pieber, T. Glasnov, C. O. Kappe, RSC Adv. 2014, 4, 13430. (c) S. E.
Baillie, T. D. Bluemke, W. Clegg, A. R. Kennedy, J. Klett, L. Russo, M.
de Tullio, E. Hevia, Chem. Commun. 2014, 50, 12859. (d) A. M. B. S. R.
C. S. Costa, F. M. Dean, M. A. Jones, D. A. Smith, R. S. Varma, J. Chem.
Soc., Chem. Commun. 1980, 1224. Also see the reference 8.
(a) A. Correa, R. Martín, J. Am. Chem. Soc. 2009, 131, 15974. (b) T.
Fujihara, K. Nogi, T. Xu, J. Terao, Y. Tsuji, J. Am. Chem. Soc. 2012, 134,
9106. (c) F. Rebih, M. Andreini, A. Moncomble, A. Harrison-Marchand, J.
Maddaluno, M. Durandetti, Chem. Eur. J. 2016, 22, 3758. (d) K.
Shimomaki, K. Murata, R. Martin, N. Iwasawa, J. Am. Chem. Soc. 2017,
139, 9467. (e) Q.-Y. Meng, S. Wang, B. König, Angew. Chem. Int. Ed.
2017, 56, 13426.
[10] (a) I. I. F. Boogaerts, S. P. Nolan, J. Am. Chem. Soc. 2010, 132, 8858.
(b) L. Zhang, J. Cheng, T. Ohishi, Z. Hou, Angew. Chem. Int. Ed. 2010,
49, 8670. (c) I. I. F. Boogaerts, G. C. Fortman, M. R. L. Furst, C. S. J.
Cazin, S. P. Nolan, Angew. Chem. Int. Ed. 2010, 49, 8674. (d) H. Inomata,
K. Ogata, S. I. Fukuzawa, Z. Hou, Org. Lett. 2012, 14, 3986. (e) H.
Mizuno, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2011, 133, 1251. (f)
T. Suga, H. Mizuno, J. Takaya, N. Iwasawa, Chem. Commun. 2014, 50,
14360. (g) T. Suga, T. Saitou, J. Takaya, N. Iwasawa, Chem. Sci. 2017,
8, 1454. (h) R. Huang, S. Li, L. Fu, G. Li, Asian J. Org. Chem. 2018, 7,
1376 (i) Z. Cai, S. Li, Y. Gao, G. Li, Adv. Synth. Catal. 2018, 18, 4005. (j)
L. Song, G.-M. Cao, W.-J. Zhou, J.-H. Ye, Z. Zhang, X.-Y. Tian, J. Li, D.-
G. Yu, Org. Chem. Front. 2018, 5, 2086. (k) L. Song, L. Zhu, Z. Zhang,
J.-H. Ye, S.-S. Yan, J.-L. Han, Z.-B. Yin, Y. Lan, D.-G. Yu, Org. Lett. 2018,
20, 3776. (l) L. Fu, S. Li, Z. Cai, Y. Ding, X.-Q. Guo, L.-P. Zhou, D. Yuan,
Q.-F. Sun, G. Li, Nat. Catal. 2018, 1, 469.
[22] (a) K. Inamoto, H. Okawa, H. Taneda, M. Sato, Y. Hirono, M. Yonemoto,
S. Kikkawa, Y. Kondo, Chem. Commun. 2012, 48, 9771. (b) K. Inamoto,
H. Okawa, S. Kikkawa, Y. Kondo, Tetrahedron, 2014, 70, 7917. (c) H.
Taneda., K. Inamoto, Y. Kondo, Chem. Commun. 2014, 50, 6523. (d) M.
Shigeno, Y. Fujii, A. Kajima, K. Nozawa-Kumada, Y. Kondo, Org.
Process Res. Dev. 2018, DOI: 10.1021/acs.oprd.8b00247. Also see, (e)
M. Shigeno, Y. Kai, T. Yamada, K. Hayashi, K. Nozawa-Kumada, C.
Denneval, Y. Kondo, Asian J. Org. Chem. 2018, 7, 2082.
[23] Wang, Zhang, Uchiyama, and co-workers recently showed that use of
both LiO-t-Bu and CsF was much effective for the t-butyl ether formation
of an aryl ammonium salt as compared with the case of using only LiO-
t-Bu. See, (a) D.-Y. Wang, Z.-K. Yang, C. Wang, A. Zhang, M. Uchiyama,
Angew. Chem. Int. Ed. 2018, 57, 3641. Also see, (b) L. A. Oparina, S. I.
Shaikhudinova, L. N. Parshina, O. V. Vysotskaya, Th. Preiss, J.
Henkelmann, B. A. Trofimov, Russ. J. Org. Chem. 2005, 41, 656.
[24] Addition of CsF was effective to increase the product yield in the
reactions of LiO-t-Bu and NaO-t-Bu (Table 1, entry 2; Table S2, entry 2).
This is probably because the cation exchange between LiO-t-Bu or NaO-
t-Bu and CsF efficiently occurs to generate stronger Brønsted base CsO-
t-Bu along with stable salt LiF or NaF. See the reference 23b.
[11] (a) G. A. Olah, B. Török, J. P. Joschek, I. Bucsi, P. M. Esteves, G. Rasul,
G. K. S. Prakash, J. Am. Chem. Soc. 2002, 124, 11379. (b) K. Nemoto,
H. Yoshida, N. Egusa, N. Morohashi, T. Hattori, J. Org. Chem. 2010, 75,
7855. (c) K. Nemoto, S. Onozawa, M. Konno, N. Morohashi, T. Hattori,
Bull. Chem. Soc. Jpn. 2012, 85, 369. (d) K. Nemoto, S. Tanaka, M.
Konno, S. Onozawa, M. Chiba, Y. Tanaka, Y. Sasaki, R. Okubo, T.
Hattori, Tetrahedron 2016, 72, 734. (e) S. Tanaka, K. Watanabe, Y.
Tanaka, T. Hattori, Org. Lett. 2016, 18, 2576. (f) K. Nemoto, H. Yoshida,
Y. Suzuki, N. Morohashi, T. Hattori, Chem. Lett. 2006, 35, 820.
[12] A limited number of papers demonstrated the direct carboxylation of
(hetero)arenes with CBr bond tolerance in the presence of a transition
metal catalyst. See references 10b, 10d, and 10h. Also see, K. Sasano,
J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2013, 135, 10954.
[25] KO-t-Bu with 18-crown-6 formed 2a-H in a good yield of 75% (Table S2,
entry 7), which was significantly higher than the cases using LiO-t-Bu or
NaO-t-Bu (Table 1, entry 3; Table S2, entry 3). This is due to the strong
complexation of potassium cation with 18-crown-6. See, (a) H. K.
Frensdorff, J. Am. Chem. Soc. 1971, 93, 600. (b) J. W. Steed, J. L.
Atwood, Supramolecular Chemistry, Second Edition, Wiley, Chichester,
UK, 2009.
[26] The present regioselectivity of CH bond at the 2-position in 1a is
different from that observed in the Lewis acid (EtAlCl2)-mediated
carboxylation at the 3-position. See the reference 11c.
[13] A CBr bond was reported to be cleaved by Lewis acids, see references
11a and 11b. Lewis-acid-mediated-carboxylations of (hetero)arenes
bearing a CBr bond afforded the products in low to moderate yields in
most cases. See references 11b-11d.
[27] Use of N,N-dimethylformamide (DMF) as a solvent also formed 2a in a
high yield of 90%, while those of o-xylene or diglyme afforded 2a-H in
middle yields of 62% and 63%, respectively (Table S3). Dimethyl
sulfoxide (DMSO), N-methylpyrrolidone (NMP), and dibutyl ether yielded
2a-H in low yields of 2%, 15%, and 3%, respectively.
[14] Only in the two reports of the transition-metal-catalyzed carboxylations
of aromatic compounds bearing benzylic alcohol-OH or benzamide-NH
moieties as a directing group, the compatibility of a ketone moiety was
demonstrated. See references 10j and 10k.
[28] In this study, the reaction was set up in a glove box. However, it was
confirmed that the carboxylation of 1a can be performed using the
standard Schlenk techniques without glove box to afford 2a in 93% yield
(Scheme S1).
[15] J. Luo, S. Preciado, P. Xie, I. Larrosa, Chem. Eur. J. 2016, 22, 6798.
[16] (a) W.-J. Yoo, M. G. Capdevila, X. Du, S. Kobayashi, Org. Lett. 2012, 14,
5326. (b) W.-J. Yoo, T. V. Q. Nguyen, M. G. Capdevila, S. Kobayashi,
Heterocycles 2015, 90, 1196.
[29] Quantitative elemental analysis of the reaction mixture of 2a-H was
performed by ICP-MS in order to understand the effects of trace metal
impurities (Table S4). The amounts of transition metals (Co, Ni, Cu, Ru,
Rh, Pd, Ag, Ir, Pt, and Au) were less than 0.2 ppm except for Fe (3.1
ppm). When the reaction of 1a was conducted in the presence of a
transition metal catalyst (20 mol %), such as Fe(OAc)2, NiCl2, Cu(OAc)2,
[RuCl(p-cymene)]2, [RhCl(cod)]2, Pd(OAc)2, or CoBr2, the yield of 2a-H
was similar to or lower than that obtained in the absence of the catalysts
[17] O. Vechorkin, N. Hirt, X. Hu, Org. Lett. 2010, 12, 3567.
[18] S. Fenner, L. Ackermann, Green Chem. 2016, 18, 3804.
[19] (a) A. Banerjee, G. R. Dick, T. Yoshino, M. W. Kanan, Nature 2016, 531,
215. (b) G. R. Dick, A. D. Frankhouser, A. Banerjee, M. W. Kanan, Green
Chem. 2017, 19, 2966. (c) K. Kudo, M. Shima, Y. Kume, F. Ikoma, S.
Mori, N. Sugita, Sekiyu Gakkaishi, 1995, 38, 40.
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