Edge Article
Chemical Science
K. Yamazaki, Y. Ano and N. Chatani, ACS Catal., 2021, 11,
Conflicts of interest
5463–5471.
There are no conicts to declare.
4 (a) A. Suzuki, Angew. Chem., Int. Ed., 2011, 50, 6723–6737; (b)
I. P. Beletskaya, F. Alonso and V. Tyurin, Coord. Chem. Rev.,
2
019, 385, 137–173; (c) H. B. Chandrashekar, A. Maji,
G. Halder, S. Banerjee, S. Bhattacharyya and D. Maiti,
Chem. Commun., 2019, 55, 6201–6204; (d)
Acknowledgements
This work was supported by a Grant in Aid for Specially
Promoted Research by MEXT (17H06091). S. R. wishes to
expresses his special thanks for a JSPS Postdoctoral Research
Fellowship. We also wish to thank the Instrumental Analysis
Centre, Faculty of Engineering, Osaka University, for assistance
with the HRMS.
H. B. Chandrashekar, P. Dolui, B. Li, A. Mandal, H. Liu,
S. Guin, H. Ge and D. Maiti, Angew. Chem., Int. Ed., 2021,
DOI: 10.1002/anie.202105204.
5 For importance of 2-pyrimidylaniline moiety, see: (a)
E. Weisberg, P. Manley, J. Mestan, S. Cowan-Jacob, A. Ray
and J. D. Griffin, Br. J. Cancer, 2006, 94, 1765–1769; (b)
T. Panneer Selvam, C. Richa James, P. V. Dniandev and
S. Karyn Valzita, Res. Pharm., 2012, 2, 1–9; (c) R. S. Dongre,
A. R. Bhat and J. S. Meshram, Am. J. PharmTech Res., 2014,
4, 138–155; (d) R. Kaur, P. Kaur, S. Sharma, G. Singh,
S. Mehndiratta, P. M. S. Bedi and K. Nepali, Recent Pat.
Anti-Cancer Drug Discovery, 2015, 10, 23–71; (e) S. Kumar,
A. Deep and B. Narasimhan, Cent. Nerv. Syst. Agents Med.
Chem., 2015, 15, 5–10.
References
1
For selected recent reviews on transition metal-catalysed
directed C–H bond functionalization, see: (a) C. Sambiagio,
D. Sch ¨o nbauer, 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. Schn u¨ rch, Chem. Soc. Rev.,
2
018, 47, 6603–6743; (b) A. Dey, S. K. Sinha, T. K. Achar
and D. Maiti, Angew. Chem., Int. Ed., 2019, 58, 10820–
0843; (c) P. Gandeepan, T. M u¨ ller, D. Zell, G. Cera,
S. Warratz and L. Ackermann, Chem. Rev., 2019, 119, 2192–
6 For reports on metal-free C–H borylation of in-built
heterocyclic compounds, see: (a) R. L. Letsinger and
D. B. MacLean, J. Am. Chem. Soc., 1963, 85, 2230–2236; (b)
F. A. Davis and M. J. S. Dewar, J. Am. Chem. Soc., 1968, 90,
3511–3515; (c) N. Ishida, T. Moriya, T. Goya and
M. Murakami, J. Org. Chem., 2010, 75, 8709–8712; (d)
Z. Zhao, Z. Chang, B. He, B. Chen, C. Deng, P. Lu, H. Qiu
and B. Z. Tang, Chem.–Eur. J., 2013, 19, 11512–11517; (e)
J. Chen, R. A. Lalancette and F. Ja, Organometallics, 2013,
32, 5843–5851; (f) D. L. Crossley, I. A. Cade, E. R. Clark,
A. Escande, M. J. Humphries, S. M. King, I. Vitorica-
Yrezabal, M. J. Ingleson and M. L. Turner, Chem. Sci., 2015,
6, 5144–5151; (g) A. C. Shaikh, D. S. Ranade, S. Thorat,
A. Maity, P. P. Kulkarni, R. G. Gonnade, P. Munshi and
N. T. Patil, Chem. Commun., 2015, 51, 16115–16118; (h)
M. Yusuf, K. Liu, F. Guo, R. A. Lalancette and F. J ¨a kle, Dalt.
Trans., 2016, 45, 4580–4587; (i) D. L. Crossley, I. Vitorica-
Yrezabal, M. J. Humphries, M. L. Turner and
M. J. Ingleson, Chem.–Eur. J., 2016, 22, 12439–12448; (j)
D. L. Crossley, L. Urbano, R. Neumann, S. Bourke, J. Jones,
L. A. Dailey, M. Green, M. J. Humphries, S. M. King,
M. L. Turner and M. J. Ingleson, ACS Appl. Mater.
Interfaces, 2017, 9, 28243–28249; (k) K. Liu, R. A. Lalancette
and F. J ¨a kle, J. Am. Chem. Soc., 2017, 139, 18170–18173; (l)
B. P. Dash, I. Hamilton, D. J. Tate, D. L. Crossley, J. S. Kim,
M. J. Ingleson and M. L. Turner, J. Mater. Chem. C, 2019, 7,
718–724; (m) S. A. Iqbal, K. Yuan, J. Cid, J. Pahl and
M. J. Ingleson, Org. Biomol. Chem., 2021, 19, 2949–2958.
7 For reports on metal-free C–H borylation directed by
removable auxiliary, see: (a) L. Niu, H. Yang, R. Wang and
H. Fu, Org. Lett., 2012, 14, 2618–2621; (b) C. Cazorla,
T. S. De Vries and E. Vedejs, Org. Lett., 2013, 15, 984–987;
(c) S. A. Iqbal, J. Cid, R. J. Procter, M. Uzelac, K. Yuan and
M. J. Ingleson, Angew. Chem., Int. Ed., 2019, 58, 15381–
15385; (d) J. Lv, X. Chen, X.-S. Xue, B. Zhao, Y. Liang,
M. Wang, L. Jin, Y. Yuan, Y. Han, Y. Zhao, Y. Lu, J. Zhao,
1
2452; (d) S. Rej, Y. Ano and N. Chatani, Chem. Rev., 2020,
120, 1788–1887; (e) J. I. Highamand and J. A. Bull, Org.
Biomol. Chem., 2020, 18, 7291–7315; (f) S. Rej, A. Das and
N. Chatani, Coord. Chem. Rev., 2021, 431, 213683.
2
For papers on transition metal-catalyzed directed C–H bond
alkylation of 2-pyrimidylanilines, see: (a) N. K. Mishra,
M. Choi, H. Jo, Y. Oh, S. Sharma, S. H. Han, T. Jeong,
S. Han, S.-Y. Lee and I. S. Kim, Chem. Commun., 2015, 51,
17229–17232; (b) G.-D. Tang, C.-L. Pan and X. Li, Org.
Chem. Front., 2016, 3, 87–90; (c) Z. Ruan, S. Lackner and
L. Ackermann, Angew. Chem., Int. Ed., 2016, 55, 3153–3157;
(
2
d) S. Allu, M. Ravi and K. C. K. Swamy, Eur. J. Org. Chem.,
016, 5697–5705; (e) Z. Ruan, D. Ghorai, G. Zanoni and
L. Ackermann, Chem. Commun., 2017, 53, 9113–9116; (f)
D. Ghorai, L. H. Finger, G. Zanoni and L. Ackermann, ACS
Catal., 2018, 8, 11657–11662.
3
For selected papers on transition metal-catalyzed directed
C–H bond functionalization of 2-pyrimidylanilines, see: (a)
W. Song and L. Ackermann, Chem. Commun., 2013, 49,
6638–6640; (b) Z. Ruan, S. Lackner and L. Ackermann, ACS
Catal., 2016, 6, 4690–4693; (c) G.-D. Tang, C.-L. Pan and
F. Xie, Org. Biomol. Chem., 2016, 14, 2898–2904; (d)
T. M u¨ ller and L. Ackermann, Chem.–Eur. J., 2016, 22,
14151–14154; (e) H. Jiang, S. Gao, J. Xu, X. Wu, A. Lin and
H. Yao, Adv. Synth. Catal., 2016, 358, 188–194; (f) Z. Ruan,
S. Lackner and L. Ackermann, Angew. Chem., Int. Ed., 2016,
55, 3153–3157; (g) L. Wang, Z. Yang, M. Yang, R. Zhang,
C. Kuai and X. Cui, Org. Biomol. Chem., 2017, 15, 8302–
8
2
307; (h) M. K. Manna, G. Bairy and R. Jana, J. Org. Chem.,
018, 83, 8390–8400; (i) S. M. Khake and N. Chatani, Org.
Lett., 2020, 22, 3655–3660; (j) H. Shen, T. Liu, D. Cheng,
X. Yi, Z. Wang, L. Liu, D. Song, F. Ling and W. Zhong, J.
Org. Chem., 2020, 85, 13735–13746; (k) S. M. Khake,
©
2021 The Author(s). Published by the Royal Society of Chemistry
Chem. Sci.