RSC Advances
Paper
This reaction proceeds in highly regioselectivity by identifying
8-aminoquinoline as the efficient bidentate directing group
embedded on the starting (hetero)arenes. Enabling a diversity
of primary and secondary carboxylic acids as well as various
benzamide derivatives as the cross-coupling substrates, our
strategy reveals its promising utility in synthetic chemistry.
5 The selective reviews on metal-catalyzed directed alkylation
of (hetero)arenes, see: (a) D. A. Colby, R. G. Bergman and
J. A. Ellman, Chem. Rev., 2010, 110, 624; (b) L. Ackermann,
Chem. Commun., 2010, 46, 4866; (c) G. Rouquet and
N. Chatani, Angew. Chem., Int. Ed., 2013, 52, 11726; (d)
F. Zhang and D. R. Spring, Chem. Soc. Rev., 2014, 43, 6906;
(e) M. Zhang, Y. F. Zhang, X. M. Jie, H. Q. Zhao, G. Li and
W. P. Su, Org. Chem. Front., 2014, 1, 843; (f) O. Daugulis,
J. Roane and L. D. Tran, Acc. Chem. Res., 2015, 48, 1053; (g)
Z. Dong, Z. Ren, S. J. Thompson, Y. Xu and G. Dong, Chem.
Rev., 2017, 117, 9333; (h) G. Zhang, F. Jia and L. J. Goossen,
Chem, 2018, 24, 4537; (i) N. Chatani, Bull. Chem. Soc. Jpn.,
2018, 91, 211; (j) C. Sambiagio, D. Schonbauer, R. Blieck,
T. Dao-Huy, G. Pototschnig, P. Schaaf, T. Wiesinger,
M. F. Zia, J. Wencel-Delord, T. Besset, B. U. W. Maes and
M. Schnurch, Chem. Soc. Rev., 2018, 47, 6603; (k)
T. Bhattacharya, S. Pimparkar and D. Maiti, RSC Adv.,
2018, 8, 19456; (l) P. Gandeepan and L. Ackermann, Chem,
2018, 4, 199; (m) G. Evano and C. Theunissen, Angew.
Chem., Int. Ed., 2019, 58, 7202; (n) S. Rej, Y. Ano and
N. Chatani, Chem. Rev., 2020, 120, 1788; (o) S. B. Ankade,
A. B. Shabade, V. Soni and B. Punji, ACS Catal., 2021, 11,
3268; (p) T. Yamaguqi, S. Natsui, K. Shibata, K. Yamazaki,
S. Rej, Y. Ano and N. Chatani, Chem.–Eur. J., 2019, 25, 6915.
6 The selective examples of decarbonylative cross-coupling
with anhydrides or carboxylic acids, see: (a) E. M. O'Brien,
E. A. Bercot and T. Rovis, J. Am. Chem. Soc., 2003, 125,
10498; (b) W. Jin, Z. Yu, W. He, W. Ye and W. J. Xiao, Org.
Lett., 2009, 11, 1317; (c) F. Pan, Z. Q. Lei, H. Wang, H. Li,
J. Sun and Z. J. Shi, Angew. Chem., Int. Ed., 2013, 52, 2063;
(d) Z.-Q. Lei, J.-H. Ye, J. Sun and Z.-J. Shi, Org. Chem. Front.,
2014, 1, 634; (e) L. Zhang, X. Xue, C. Xu, Y. Pan, G. Zhang,
L. Xu, H. Li and Z. Shi, ChemCatChem, 2014, 6, 3069; (f)
C. Liu, C. L. Ji, X. Hong and M. Szostak, Angew. Chem., Int.
Ed., 2018, 57, 16721; (g) X. Qiu, P. Wang, D. Wang,
M. Wang, Y. Yuan and Z. Shi, Angew. Chem., Int. Ed., 2019,
58, 1504; (h) H. Zhao, X. Xu, H. Yu, B. Li, X. Xu, H. Li,
L. Xu, Q. Fan and P. J. Walsh, Org. Lett., 2020, 22, 4228.
7 The studies on ortho-substituent effect on metal-catalyzed
decarboxylation, see: (a) J. Cornella, C. Sanchez, D. Banawa
and I. Larrosa, Chem. Commun., 2009, 46, 7176; (b) L. Xue,
W. Su and Z. Lin, Dalton Trans., 2011, 40, 11926; (c)
R. Grainger, J. Cornella, D. C. Blakemore, I. Larrosa and
J. M. Campanera, Chem.–Eur. J., 2014, 20, 16680.
Conflicts of interest
There are no conicts to declare.
Acknowledgements
This work was supported by the National Key Research and
Development Program of China (2018YFA0704502), the
National Natural Science Foundation of China (Grants No.
21931011, 22071241), the Strategic Priority Research Program of
the Chinese Academy of Sciences (XDB20000000 and
XDB10040304), and the Key Research Program of Frontier
Sciences, CAS (QYZDJ-SSW-SLH024).
Notes and references
1 For selective reviews on C–H alkyaltion, see: (a)
W. R. Gutekunst and P. S. Baran, Chem. Soc. Rev., 2011, 40,
1976; (b) J. Yamaguchi, A. D. Yamaguchi and K. Itami,
Angew. Chem., Int. Ed., 2012, 51, 8960; (c) E. J. E. Caro-Diaz,
M. Urbano, D. J. Buzard and R. M. Jones, Bioorg. Med.
Chem. Lett., 2016, 26, 5378; (d) G. Evano and
C. Theunissen, Angew. Chem., Int. Ed., 2019, 58, 7558.
2 (a) R. M. Roberts and A. A. Khalaf, Friedel-Cras Alkylation
Chemistry: A Century of Discovery, Marcel Dekker, New York,
1984; (b) M. Bandini, A. Melloni and A. Umani-Ronchi,
Angew. Chem., Int. Ed., 2004, 43, 550; (c) T. B. Poulsen and
K. A. Jorgensen, Chem. Rev., 2008, 108, 2903.
3 For selective reviews on oxidative decarboxylative cross-
coupling of alkyl carboxylic acids, see: (a) J. Xuan,
Z. G. Zhang and W. J. Xiao, Angew. Chem., Int. Ed., 2015,
54, 15632; (b) M. O. Konev and E. R. Jarvo, Angew. Chem.,
Int. Ed., 2016, 55, 11340; (c) P. Liu, G. Zhang and P. Sun,
Org. Biomol. Chem., 2016, 14, 10763; (d) H. Bao, Y. Li, L. Ge
and M. Muhammad, Synthesis, 2017, 49, 5263; (e) T. Patra
and D. Maiti, Chem, 2017, 23, 7382.
4 The selective examples of oxidative decarboxylative cross-
coupling of alkyl carboxylic acids, see: (a) F. Yin, Z. Wang,
Z. Li and C. Li, J. Am. Chem. Soc., 2012, 134, 10401; (b)
M. Rueda-Becerril, O. Mahe, M. Drouin, M. B. Majewski,
J. G. West, M. O. Wolf, G. M. Sammis and J. F. Paquin, J.
Am. Chem. Soc., 2014, 136, 2637; (c) Z. Zuo, D. T. Ahneman,
L. Chu, J. A. Terrett, A. G. Doyle and D. W. MacMillan,
Science, 2014, 345, 437; (d) Q. Q. Zhou, W. Guo, W. Ding,
X. Wu, X. Chen, L. Q. Lu and W. J. Xiao, Angew. Chem., Int.
Ed., 2015, 54, 11196; (e) Z. J. Liu, X. Lu, G. Wang, L. Li,
W. T. Jiang, Y. D. Wang, B. Xiao and Y. Fu, J. Am. Chem.
Soc., 2016, 138, 9714; (f) C. P. Johnston, R. T. Smith,
S. Allmendinger and D. W. MacMillan, Nature, 2016, 536,
322.
8 The selective examples of 8-aminoquinoline-directed C–H
functionalization, see: (a) V. G. Zaitsev, D. Shabashov and
O. Daugulis, J. Am. Chem. Soc., 2005, 127, 13154; (b)
Y. Aihara and N. Chatani, J. Am. Chem. Soc., 2013, 135,
5308; (c) S. Asako, L. Ilies and E. Nakamura, J. Am. Chem.
Soc., 2013, 135, 17755; (d) W. Song, S. Lackner and
L. Ackermann, Angew. Chem., Int. Ed., 2014, 53, 2477; (e)
E. R. Fruchey, B. M. Monks and S. P. Cook, J. Am. Chem.
Soc., 2014, 136, 13130; (f) L. Ilies, T. Matsubara,
S. Ichikawa, S. Asako and E. Nakamura, J. Am. Chem. Soc.,
2014, 136, 13126; (g) B. M. Monks, E. R. Fruchey and
S. P. Cook, Angew. Chem., Int. Ed., 2014, 53, 11065; (h)
S. Y. Zhang, Q. Li, G. He, W. A. Nack and G. Chen, J. Am.
19830 | RSC Adv., 2021, 11, 19827–19831
© 2021 The Author(s). Published by the Royal Society of Chemistry