Organic Letters
Letter
C, K.; Kumar CH, V.; Sular G, M.; Sumathi, S. Tetrahedron Lett. 2015,
56, 3799.
(9) Hie, L.; Fine Nathel, N. F.; Hong, X.; Yang, Y.-F.; Houk, K. N.;
Garg, N. K. Angew. Chem., Int. Ed. 2016, 55, 2810−2814.
(10) Ortega, N.; Richter, C.; Glorius, F. Org. Lett. 2013, 15, 1776−
1779.
In conclusion, a highly efficient protocol using [Ni(quin)2]
has been developed with imidazole as homogeneous medium
for N-formylation and N-acylation of aliphatic, aromatic, and
heterocyclic amines. The advantages of the present protocol are
moderate to excellent yields, no requirement of inert
atmosphere, easy workup, and purification procedures.
(11) Liu, H. Q.; Liu, J.; Zhang, Y. H.; Shao, C. D.; Yu, J. X. Chin.
Chem. Lett. 2015, 26, 11−14.
ASSOCIATED CONTENT
́
(12) Becerra-Figueroa, L.; Ojeda-Porras, A.; Gamba-Sanchez, D. J.
■
Org. Chem. 2014, 79, 4544−4552.
S
* Supporting Information
(13) Gu, D. W.; Guo, X. X. Tetrahedron 2015, 71, 9117−9122.
(14) Chandrashekhar, A.; Ravikumar, A.; Sathaiah, G.; Lukepaul, V.;
Sridhar, M.; Shanthanrao, P. Tetrahedron Lett. 2009, 50, 7099−7101.
(15) Hosseini-Sarvari, M.; Sharghi, H. J. Org. Chem. 2006, 71, 6652−
6654.
The Supporting Information is available free of charge on the
Experimental procedures, characterization of compounds
2a−u, 3a−n, and catalyst [Ni(quin)2] (1H and 13C NMR
spectra), optimization table, and X-ray diffraction data for
ligand (8-hydroxyquinoline), catalyst [Ni(quin)2], and
(16) Shah, N.; Gravel, E.; Jawale, D. V.; Doris, E.; Namboothiri, N.
N. I. ChemCatChem 2014, 6, 2201−2205.
(17) Kim, J. − G.; Jang, D. O. Synlett 2010, 2010, 1231−1234.
(18) Sajadi, S. M.; Maham, M.; Rezaei, A. Lett. Org. Chem. 2014, 11,
49−54.
(19) Kim, Y. J.; Lee, J. W.; Lee, H. J.; Zhang, S.; Lee, J. S.; Cheong,
M.; Kim, H. S. Appl. Catal., A 2015, 506, 126−133.
(20) Chen, Z.; Fu, R.; Chai, W.; Zheng, H.; Sun, L.; Lu, Q.; Yuan, R.
Tetrahedron 2014, 70, 2237−2245.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
(21) Nirmala, M.; Prakash, G.; Viswanathamurthi, P.; Malecki, J. G. J.
Mol. Catal. A: Chem. 2015, 403, 15−26.
(22) Karami, B.; Farahi, M.; Pam, F. Tetrahedron Lett. 2014, 55,
6292−6296.
Notes
(23) Rasheed, Sk.; Rao, D. N.; Reddy, A. S.; Shankar, R.; Das, P. RSC
Adv. 2015, 5, 10567−10574.
(24) Pathare, S. P.; Sawant, R. V.; Akamanchi, K. G. Tetrahedron Lett.
2012, 53, 3259−3263.
The authors declare no competing financial interest.
(25) (a) Joseph, S.; Das, P.; Srivastava, B.; Nizar, H.; Prasad, M.
Tetrahedron Lett. 2013, 54, 929−931. (b) Gerack, C. J.; McElwee-
White, L. Molecules 2014, 19, 7689−7713. (c) Shastri, L. A.; Shastri, S.
L.; Bathula, C. D.; Basanagouda, M.; Kulkarni, M. V. Synth. Commun.
2011, 41, 476−484. (d) Allen, C. L.; Williams, J. M. J. Chem. Soc. Rev.
2011, 40, 3405−3415.
ACKNOWLEDGMENTS
■
We thank Baburaoji Gholap Research Center for support.
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