PANDA ET AL.
9 of 10
Chem. Soc. 1992, 114, 8863; j) Y. Yamamoto, R. Fujikawa,
T. Umemoto, N. Miyaura, Tetrahedron 2004, 60, 10695;
k) S. P. Thomas, V. K. Aggarwal, Angew Chem Int Ed 2009, 48,
1896; l) L. Zhang, Z. Zuo, X. Leng, Z. Huang, Angew Chem Int
Ed 2014, 53, 2696; m) A. Bismuto, M. J. Cowley, S. P. Thomas,
ACS Catal. 2018, 8, 2001; n) K. Nakajima, T. Kato,
Y. Nishibayash, Org. Lett. 2017, 19, 4323.
REFERENCES
[1] S. A. Lawrence, Amines: Synthesis, Properties and Applications,
Cambridge, Cambridge University Press 2005.
[2] a) K. Eller, E. Henkes, R. Rossbacher, H. Höke, Aliphatic
Amines. In Ullmann's Encyclopedia of Industrial Chemistry,
7th ed. Vol. 2, Wiley-VCH, Weinheim, Germany 2008;
b) L. A. Oro, D. Carmona, J. M. Fraile, in Metal-Catalysis
in Industrial Organic Processes, (Eds: G. P. Chiusoli,
P. M. Maitlis) Vol. 79, RSC Publishing, London 2006;
c) J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Bio-
mol. Chem. 2006, 4, 2337; d) A. Ricci, Modern Amination
Methods, Wiley, Weinheim 2000; e) K. Hayes, Appl. Catal., a
2001, 221, 187.
[9] a) H. Ben-Daat, C. L. Rock, M. Flores, T. L. Groy,
A. C. Bowman, R. J. Trovitch, Chem Commun 2017, 53, 7333;
b) J. E. Lee, J. Kwon, J. Yun, Chem Commun 2008, 6, 733;
c) H. R. Kim, I. G. Jung, K. Yoo, K. Jang, E. S. Lee, J. Yun,
S. U. Son, Chem Commun 2010, 46, 758; d) H. R. Kim, J. Yun,
Chem Commun 2011, 47, 2943; e) C. Gunanathan,
M. Holscher, F. Pan, W. Leitner, J. Am. Chem. Soc. 2012, 134,
14349; f) S. R. Tamang, M. Findlater, J Org Chem 2017, 82,
12857; g) R. Arévalo, C. M. Vogels, G. A. MacNeil, L. Riera,
J. Pérez, S. A. Westcott, Dalton Trans 2017, 46, 7750;
h) S. Chen, D. Yan, M. Xue, Y. Hong, Y. Yao, Q. Shen, Org.
Lett. 2017, 19, 3382; i) A. A. Oluyadi, S. Ma, C. N. Muhoro,
Organometallics 2013, 32, 70; j) W. Wang, X. Shen, F. Zhao,
H. Jiang, W. Yao, S. A. Pullarkat, L. Xu, M. Ma, J Org Chem
2018, 83, 69; k) J. Guo, J. Chen, Z. Lu, Chem Commun 2015,
51, 5725.
[3] N. Fleury-Brégeot, V. D. L. Fuente, S. Castillón, C. Claver,
ChemCatChem 2010, 2, 1346.
[4] a) R. O. Hutchins, M. K. Hutchins, in Comprehensive Organic
Synthesis, (Eds: B. M. Trost, I. Fleming) Vol. 8, Pergamon
Press, Oxford, U.K. 199125; b) J. SeydenPenne, Reductions by
the Alumino- and Borohydrides in Organic Synthesis, 2nd
ed. Vol. 122, Wiley-VCH, Inc., New York 1997; c) M. P. Boone,
D. W. Stephan, J. Am. Chem. Soc. 2013, 135, 8508; d) P. Ji,
K. Manna, Z. Lin, A. Urban, F. X. Greene, G. Lan, W. Lin,
J. Am. Chem. Soc. 2016, 138, 12234; e) A. J. Hatnean,
J. W. Thomson, P. A. Chase, D. W. Stephan, Chem Commun
2014, 50, 301; f) J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev.
2010, 111, 1713.
[5] a) J. Seyden-Penne, Reductions by Alumino- and Borohydrides
in Organic Synthesis, 2nd ed., Wiley-VCH, New York 1997;
b) S. Nishimura, Handbook of heterogeneous catalytic hydroge-
nation for organic synthesis, Wiley-VCH, New York 2001;
c) J. G. de Vries, C. J. Elsevier, Handbook of homogeneous
hydrogenation, Wiley-VCH, Weinheim 2006.
[10] a) D. S. Matteson, in The Metal-Carbon Bond, (Ed.:
F. R. Hartley) Vol. 4, John Wiley & Sons, Inc., Chichester,
U.K. 1987307; b) M. Davidson, A. K. Hughes, T. B. Marder,
K. Wade, Contemporary Boron Chemistry, Royal Society of
Chemistry, Cambridge, U.K. 2000371; c) A. Suzuki, Angew
Chem Int Ed 2011, 50, 6722.
[11] C. C. Chong, R. Kinjo, ACS Catal. 2015, 5, 3238.
[12] See Ref. 4(f). a) M. Rueping, E. Sugiono, C. Azap,
T. Theissmann, A. P. Antonchick, S. N. Khan, N. J. Cho,
H.-S. Kim, in Regio- and Stereo- Controlled Oxidations and
Reductions, (Eds: S. M. Roberts, J. Whittall) Vol. 5, Wiley,
Hoboken 2007 Chapter 4; b) P. G. Andersson, I. J. Munslow
(Eds), Modern Reduction Methods, Wiley, Hoboken 2008;
c) M. Figlus, Recoverable Catalysts for Asymmetric Reduction of
Imines: Synthesis and Evaluation of Activities, Verlag Dr,
Müller, Saarbrücken 2010; d) J. F. Carpentier, V. Bette, Curr.
Org. Chem. 2002, 6, 913; e) O. Riant, N. Mostefai,
J. Courmarcel, Synthesis 2004, 2943; f) S. Díez-González,
S. P. Nolan, Org Prep Proc Int 2007, 39, 523; g) C. G. Arena,
Mini-Rev. Org. Chem. 2009, 6, 159; h) T. C. Nugent, M. El-
Shazly, Adv Synth Catal 2010, 352, 753; i) Z. Wang, Z. Jiang,
Asian J. Chem. 2010, 22, 4141; j) S. Guizzetti, M. Benaglia, Eur.
J. Org. Chem. 2010, 2010, 5529; k) J. G. De Vries, N. Mrsic,
Catal. Sci. Technol. 2011, 1, 727; l) Z. Yu, W. Jin, Q. Jiang,
Angew Chem Int Ed 2012, 51, 6060.
[13] See Ref. 3, 4(f), 11(h). a) W. Tang, J. Xiao, Synthesis 2014, 46,
1297; b) A. Bartoszewicz, N. Ahlsten, B. Martìn-Matute, Chem.
– Eur. J. 2013, 19, 7274; c) A. Fabrello, A. Bachelier,
M. Urrutigoïty, P. Kalck, Coord. Chem. Rev. 2010, 254, 273.
[14] R. T. Baker, J. C. Calabrese, S. A. Westcott, J. Organomet.
Chem. 1995, 498, 109.
[15] See Ref. 8(f). a) J. Wu, H. Zeng, J. Cheng, S. Zheng,
J. A. Golen, D. R. Manke, G. Zhang, J Org Chem 2018, 83,
9442; b) A. Kaithal, B. Chatterjee, C. Gunanathan, J Org Chem
2016, 81, 11153; c) D. Mukherjee, A.-K. Wiegand,
T. P. Spaniol, J. Okuda, Dalton Trans 2017, 46, 6183.
[6] H. Elsen, C. Färber, G. Ballmann, S. Harder, Angew Chem Int
Ed 2018, 57, 7156.
[7] a) L. Palacios, Y. Meheut, M. Galiana-Cameo, M. J. Artigas,
A. D. I. Giuseppe, F. J. Lahoz, V. Polo, R. Castarlenas,
J. J. Pérez-Torrente, L. A. Oro, Organometallics 2017, 36, 2198;
b) Y. Moglie, M. J. González-Soria, I. Martín-García,
G. Radivoy, F. Alonso, Green Chem. 2016, 18, 4896;
ꢀ
ꢀ
c) K. Kucinski, P. Pawluc, G. Hreczycho, Adv Synth Catal
ꢀ
ꢀ
2015, 357, 3936; d) K. Kucinski, P. Pawluc, B. Marciniec,
G. Hreczycho, Chem. – Eur. J. 2015, 21, 4940; e) Y. Nakajima,
S. Shimada, RSC Adv. 2015, 5, 20603; f) K. Kucinski,
J. Szudkowska-Frątczak, G. Hreczycho, Chem. – Eur. J. 2016,
22, 13046; g) H. Stachowiak, J. Kaźmierczak, K. Kucinski,
G. Hreczycho, Green Chem. 2018, 20, 1738.
ꢀ
[8] a) R. J. P. Corriu, J. J. E. Moreau, M. J. Pataud-Sat, Organomet.
Chem. 1982, 228, 301; b) T. Murai, T. Sakane, S. J. Kato, Org
Chem 1990, 55, 449; c) A. M. Caporusso, N. Panziera,
P. Pertici, E. Pitzalis, P. Salvadori, G. Vitulli, G. J. Martra, Mol
Catal a: Chem 1999, 150, 275; d) S. Laval, W. Dayoub,
A. FavreReguillon, M. Berthod, P. Demonchaux, G. Mignani,
M. Lemaire, Tetrahedron Lett. 2009, 50, 7005; e) S. Das,
S. Zhou, D. Addis, S. Enthaler, K. Junge, M. Beller, Top. Catal.
2010, 53, 979; f) D. Addis, S. Das, K. Junge, M. Beller, Angew
Chem Int Ed 2011, 50, 6004; g) S. Das, B. Wendt, M. Möller,
K. Junge, M. Beller, Angew Chem Int Ed 2012, 51, 1662;
h) K. Burgess, M. J. Ohlmeyer, J Org Chem 1988, 53, 5178;
i) S. A. Westcott, H. P. Blom, T. B. Marder, R. T. Baker, J. Am.