tꢉꢋꢈꢂꢋ 'ꢄ ꢇꢄꢎ ꢈ'ꢃꢅꢂꢎ ꢐꢈꢆ(ꢁꢇꢂ
Catalysis Science & Technology
Page 4 of 5
DOI: 10.1039/C8CY00859K
/haaÜbL/!ÇLhb
Wꢀꢁꢂꢃꢄꢅ bꢄꢆꢇ
9
(a) L. Blackburn and R. J. Taylor, Org. Lett., 2001,
3, 1637; (b) S.
Lꢇ ꢂꢅꢐꢐꢈꢆꢌ! ꢈꢇ ꢈꢁꢆ$ꢂꢎꢈ/ꢉꢋ! +ꢀꢄꢂ+ꢀꢁꢇꢋ$ꢏꢆꢋꢋ! ꢇꢄꢇ$+ꢆꢋꢍꢁꢄꢅꢂ
ꢍꢄ/ꢈꢉꢎ,LL-$bbb +ꢁꢇꢍꢋꢆ ꢍꢄꢐ+ꢉꢋꢓ ꢍꢈꢎꢈꢉꢌCꢋ' 'ꢁꢆꢋꢍꢎ b$ꢈꢉ?ꢌꢉꢈꢎꢁꢄꢇ ꢄꢏ
ꢈꢇꢁꢉꢁꢇꢋꢂ 2ꢁꢎꢀ ꢈꢉꢍꢄꢀꢄꢉꢂ ꢌꢆꢁ ꢀꢌ'ꢆꢄ(ꢋꢇ ꢈꢅꢎꢄ$ꢎꢆꢈꢇꢂꢏꢋꢆ ꢂꢎꢆꢈꢎꢋ(ꢌ ,I!-!
ꢈꢇ' ꢂꢋꢉꢋꢍꢎꢁ.ꢋ ꢈꢍꢍꢋ+ꢎꢄꢆꢉꢋꢂꢂ'ꢋꢀꢌ'ꢆꢄ(ꢋꢇꢈꢎꢁ.ꢋ ꢍꢄꢅ+ꢉꢁꢇ( ,!5/- ꢄꢏ
/ꢋꢇCꢌꢉ ꢈꢐꢁꢇꢋꢂ ꢄꢆ ꢈꢉ?ꢌꢉ ꢈꢐꢁꢇꢋꢂ 2ꢁꢎꢀ ꢈꢉꢍꢄꢀꢄꢉꢂ ꢈꢏꢏꢄꢆ'ꢁꢇ( ꢁꢐꢁꢇꢋꢂ
2ꢁꢎꢀ ꢎꢀꢋ ꢉꢁ/ꢋꢆꢈꢎꢁꢄꢇ ꢄꢏ ꢐꢄꢉꢋꢍꢅꢉꢈꢆ ꢀꢌ'ꢆꢄ(ꢋꢇ ꢈꢇ' 2ꢈꢎꢋꢆ ꢁꢂ
ꢆꢋ+ꢄꢆꢎꢋ' /ꢄꢇꢎꢆꢄꢉ ꢈꢇ' 'ꢋꢅꢎꢋꢆꢁꢅꢐ ꢉꢈ/ꢋꢉꢉꢁꢇ( ꢋꢓ+ꢋꢆꢁꢐꢋꢇꢎꢂ ꢂꢀꢄ2ꢋ'
ꢎꢀꢈꢎ ꢎꢀꢋ ꢁꢇꢁꢎꢁꢈꢉ 'ꢋꢀꢌ'ꢆꢄ(ꢋꢇꢈꢎꢁꢄꢇ ꢄꢏ ꢈꢉꢍꢄꢀꢄꢉ ꢁꢂ ꢆꢋ.ꢋꢆꢂꢁ/ꢉꢋ ꢈꢇ'
ꢄ+ꢋꢆꢈꢎꢋ' .ꢁꢈ !5/ ꢂꢎꢆꢈꢎꢋ(ꢌ
Sithambaram, R. Kumar, Y.-C. Son and S. L. Suib, J. Catal., 2008, 253
,
269; (c) L. Jiang, L. Jin, H. Tian, X. Yuan, X. Yu and Q. Xu, Chem.
Commun., 2011, 47, 10833; (d) J. Xu, R. Zhuang, L. Bao, G. Tang and
Y. Zhao, Green Chem., 2012, 14, 2384; (e) H. Tian, X. Yu, Q. Li, J.
Wang and Q. Xu, Adv. Synth. Catal., 2012, 354, 2671; (f) Q. Kang and
Y. G. Zhang, Green Chem., 2012, 14, 1016; (g) E. L. Zhang, H. W. Tian,
S. D. Xu, X. C. Yu and Q. Xu, Org. Lett., 2013, 15, 2704; (h) B. Chen, J.
Li, W. Dai, L. Wang and S. Gao, Green Chem., 2014, 16, 3328; (i) L.
Han, P. Xing and B. Jiang, Org. Lett., 2014, 16, 3428; (j) M. Guan, C.
Wang, J. Zhang and Y. Zhao, RSC Adv,. 2014,
4, 48777; (k) M. Tamura
and K. Tomishige, Angew. Chem. Int. Ed., 2015, 54, 864; (l) B. Chen, S.
Shang, L. Wang, Y. Zhang and S. Gao, Chem. Commun., 2016, 52
,
481.
/ꢀꢃ(ꢅꢐꢍꢑꢌ ꢀ( ꢐꢃꢑꢇꢂꢇꢌꢑ
10 (a) N.Deibl and R. Kempe, J. Am. Chem. Soc., 2016, 138, 10786; (b) A.
Mukherjee, A.Nerush, G.Leitus, L. J. W. Shimon, Y. B. David, N. A. E.
Jalapa and D. Milstein, J. Am. Chem. Soc., 2016, 138, 4298.
Çꢀꢋꢆꢋ ꢈꢆꢋ ꢇꢄ ꢍꢄꢇꢏꢉꢁꢍꢎꢂ ꢎꢄ 'ꢋꢍꢉꢈꢆꢋ
11 (a) A. Corma, J. Navas and M. J. Sabater, Chem. Rev., 2018, 118
1410; (b) U. K. Das, Y. Ben David, Y. Diskin Posner and D. Milstein,
Angew. Chem. Int. Ed. 2018, 57, 2179. (c) G. A. Filonenko, R. van
,
ꢀ
ꢀ
!ꢍꢓꢃꢀꢊꢅꢇꢕꢎꢇꢆꢇꢃꢑꢌ
Çꢀꢁꢂ ꢆꢋꢂꢋꢈꢆꢍꢀ ꢁꢂ ꢂꢅ++ꢄꢆꢎꢋ' /ꢌ ꢎꢀꢋ 9aw9ꢑꢒ"59#ꢒ ,ꢅꢇ'ꢋꢆ ꢎꢀꢋ {9w.$
Dꢆꢋꢋꢇ /ꢀꢋꢐꢁꢂꢎꢆꢌ +ꢆꢄ(ꢆꢈꢐꢐꢋ- ꢈꢇ' /{Lw$LbtwhÇL/{ ,I/tꢒꢒ""- {ta
ꢈꢇ' ëD[ ꢎꢀꢈꢇ? ꢎꢀꢋ /{Lw ꢏꢄꢆ ꢎꢀꢋ ꢆꢋꢂꢋꢈꢆꢍꢀ ꢏꢋꢉꢉꢄ2ꢂꢀꢁ+ ëa
ꢈꢍ?ꢇꢄ2ꢉꢋ'(ꢋꢂ ꢎꢀꢋ {9w. ,9aw9ꢑꢒ"D9ꢒꢒD"ꢒD- ꢈꢇ' ꢎꢀꢋ ÜD/ ,#ꢒ$
""9ꢑꢒ"5 {!,LL--
Putten, E. J. M. Hensenand E. A. Pidko, Chem. Soc. Rev., 2018, 47
,
1459.
12 (a) S. Rösler, M. Ertl, T. Irrgang and R. Kempe, Angew. Chem. Int. Ed.,
2015, 54, 15046; (b) G. Zhang, Z. Yin and S. Zheng, Org. Lett., 2016,
18, 300; (c) Z. Yin, H. Zeng, J. Wu, S. Zheng and G. Zhang, ACS Catal.,
2016,
K. Kirchner, Org. Lett., 2016, 18
Rodriguez, ChemSusChem, 2016, , 28; (f) S. P. Midya, A. Mondal, A.
6
, 6546; (d) M. Mastalir, G. Tomsu, E. Pittenauer, G. Allmaier and
,
3462; (e) A. Quintard and J.
9
bꢀꢑꢇꢌ ꢄꢃꢕ ꢂꢇ(ꢇꢂꢇꢃꢍꢇꢌ
Begum and E. Balaraman, Synthesis, 2017,3957.
13 P. Daw, Y. B. David and D. Milstein, ACS Catal., 2017, 7, 7456.
1
J. L. McGuire, Pharmaceuticals: Classes, Therapeutic Agents, Areas of
Application, Wiley-VCH: Weinheim, Germany, 2000, 1-4; (b) A. Ricci,
Amino Group Chemistry: From Synthesis to the Life Sciences, Wiley-
VCH Verlag GmbH & Co. KGaA, Weinheim 2008; (c) S. A. Lawrence,
Amines: Synthesis Properties and Applications, Cambridge University
Press, Cambridge, 2004; (d) A. Ricci, Amino Group Chemistry, From
Synthesis to the Life Sciences, Wiley-VCH, Weinheim, 2007; (e) S.
Kegnæs, J. Mielby, U. V. Mentzel, C. H. Christensen and A. Riisager,
Green Chem., 2010, 12, 1437.
14 (a) B. Gnanaprakasam, J. Zhang and David Milstein Angew. Chem. Int.
Ed. 2010, 49, 1468-1471; (b) G. Zeng and S. Li, Inorg. Chem. 2011, 50
,
10572; (c) D. Srimani, Y. Ben-David and D. Milstein, Angew. Chem., Int.
Ed. 2013, 52, 4012; (d) M. Trincado, D. Banerjee and H. Grützmacher,
Energy Environ. Sci. 2014,
7, 2464; (e) A. Maggi and R. Madsen,
Organometallics 2012, 31, 451; (f) B. Saha; S. M. WahidurRahaman, P.
Daw, G. Sengupta and J. K. Bera, Chem. -Eur. J. 2014, 20, 6542; (g) F.
Hasanayn, and H. Harb, Inorg. Chem. 2014, 53, 8334; (h) S. Ruch, T.
Irrgang and R. Kempe, Chem. -Eur. J. 2014, 20, 13279; (i) J. Bain, P.
Cho and A. Voutchkova-Kostal, Green Chem., 2015, 17, 2271; (j) T. S.
Manikandan, R. Ramesh, N. Shivalingegowda and L. N.
2
3
(a) Y. Juaand and R. S. Varma, Green Chem., 2004,
6
, 219; (b) J. C.
Castillo, J. Orrego
ꢀHernández and J. Portilla, Eur. J. Org. Chem., 2016,
22, 3824.
Krishnappagowda, ChemistrySelect, 2018, 3, 1561-1568; (k) A. Maggi
Recent selected examples of reductive alkylation: (a) I. Sorribes, K.
Junge and M. Beller, J. Am. Chem. Soc., 2014, 136, 14314; (b) A.
Volkov, F. Tinnis and H. Adolfsson, Org. Lett., 2014, 16, 680; (c) N. L.
Lampland, M. Hovey, D. Mukherjee and A. D. Sadow, ACS Catal.,
and R. Madsen, Organometallics, 2012, 31, 451. (l) M. Tamura and K.
Tomishige, Angew. Chem., Int. Ed., 2015, 54, 864; (m) B. Chen, S.
Shang, L. Wang, Y. Zhang and S. Gao, Chem. Commun., 2016, 52
,
481; (n) G. Jaiswal, V. G. Landge, D. Jagadeesan and E. Balaraman,
Green Chem., 2016, 18, 3232.
2015,
5
, 4219; (d) Z. Chen, H. Zeng, H. Gong, H. Wang and C. Li,
, 4174; (e) K. G. Andrews, D. M. Summers, L. J.
Chem. Sci., 2015,
6
15 G, Zhang and S. K. Hanson, Org. Lett., 2013, 15, 650.
16 A. Mukherjee, A. Nerush, G. Leitus, L. J. W. Shimon, Y. Ben David, N.
A. E. Jalapa and David Milstein, J. Am. Chem. Soc. 2016, 138, 4298.
Donnelly and R. M. Denton, Chem. Commun., 2016, 52, 1855.
4
(a) T. E. Müller, K. C. Hultzsch, M.Yus, F. Foubelo and M. Tada, Chem.
Rev., 2008, 108, 3795; (b) L. Huang, M. Arndt, K.Gooßen, H. Heydt and
L. J. Gooßen, Chem. Rev., 2015, 115, 2596; (c) S. Zhu, N. Niljianskul
and S. L. Buchwald, Nat. Chem., 2016,
(a) S. Raoufmoghaddam, Org. Biomol. Chem., 2014, 12, 7179; (b) D.
Crozet, M. Urrutigoïty and P. Kalck, ChemCatChem., 2011, , 1102.
8, 144.
5
6
3
(a)K. C. Nicolaou, C. J. N. Mathison and T. Montagnon, Angew. Chem.,
Int. Ed., 2003, 42, 4077; (b) K. C. Nicolaou, C. J. N. Mathison and T.
Montagnon, J. Am. Chem. Soc., 2004, 126, 5192; (c) P. Fontaine, A.
Chiaroni, G. Masson and J. Zhu, Org. Lett., 2008, 10, 1509.
7
8
(a) B. Chen, L. Wang, W. Dai, S. Shang, Y. Lv and S. Gao, ACS Catal.,
2015,
5
, 2788; (b) S. Biswas, B. Dutta, K. Mullick, C.-H. Kuo, A. S.
, 4394; (c) R. Kumar, E. H.
Poyraz and S. L. Suib, ACS Catal., 2015,
5
Gleissner, E. G. V. Tiu and Y. Yamakoshi, Org. Lett., 2016, 18, 184; (d)
R. E. Rodríguez-Lugo, M. A. Chacón-Terán, S. De León, M. Vogt, A.
J.Rosenthald and V. R. Landaeta, Dalton Trans., 2018, 47, 2061.
(a) R.Severina and Sven Doye, Chem. Soc. Rev., 2007, 36, 1407; (b) J.
Zhao, Z. Zheng, S. Bottle, A. Chou, S. Sarina and H. Zhu, Chem.
Commun., 2013, 49, 2676; (c) L. Lee and Y. Zhao, ACS Catal., 2014, 4,
688.
+ % Wꢀ bꢁꢂꢃ ! ꢑꢒ"ꢑ! ꢈꢈ! "$#
Çꢀꢁꢂ ꢃꢄꢅꢆꢇꢈꢉ ꢁꢂ ꢊ Çꢀꢋ wꢄꢌꢈꢉ {ꢄꢍꢁꢋꢎꢌ ꢄꢏ /ꢀꢋꢐꢁꢂꢎꢆꢌ ꢑꢒꢓꢓ
tꢉꢋꢈꢂꢋ 'ꢄ ꢇꢄꢎ ꢈ'ꢃꢅꢂꢎ ꢐꢈꢆ(ꢁꢇꢂ
Midya, Siba P.
