Green Chemistry
Communication
Chem.,
2005,
48,
2274–2277;
(b)
C.
Fotsch,
genated solvents or DMF, which is 80% of all reported reac-
tions in the database. Search conducted December 5th
2016.
J. D. Sonnenberg, N. Chen, C. Hale, W. Karbon and
M. H. Norman, J. Med. Chem., 2001, 44, 2334–2356.
6 (a) H.-Q. Li, P.-C. Lv, T. Yan and H.-L. Zhu, Anti-Cancer 20 For a recent example of the use of bio-alternative solvents
Agents Med. Chem., 2009, 9, 417–480; (b) H. Gurulingappa,
M. L. Amador, M. Zhao, M. A. Rudek, M. Hidalgo and
S. R. Khan, Bioorg. Med. Chem. Lett., 2004, 14, 2213–2216.
7 A. A. Bastian, A. Marcozzi and A. Herrmann, Nat. Chem.,
2012, 11, 789–793.
in synthesis, see: D. Rasina, A. Lombi, S. Santoro, F. Ferlin
and L. Vaccaro, Green Chem., 2016, 18, 6380–6386.
21 D. J. C. Constable, P. J. Dunn, J. D. Hayler, G. R. Humphrey,
J. L. Leazer Jr., R. J. Linderman, R. J. Lorenz, K. Manley,
B. A. Pearlman, A. Wells, A. Zaks and T. Y. Zhang, Green
Chem., 2007, 9, 411–420.
8 D. Kaufmann, M. Bialer, J. A. Shimshoni, M. Devor and
B. Yagen, J. Med. Chem., 2009, 52, 7236–7248.
22 For recent publications on the use of more sustainable sol-
vents and solvent selection guides, see: (a) D. Prat,
A. Wells, J. Hayler, H. Sneddon, C. R. McElroy, S. Abou-
Shehada and P. J. Dunn, Green Chem., 2016, 18, 288–296;
(b) F. P. Byrne, S. Jin, G. Paggiola, T. H. M. Petchey,
J. H. Clark, T. J. Farmer, A. J. Hunt, C. R. McElroy and
J. Sherwood, Sustainable Chem. Processes, 2016, 4(7), DOI:
10.1186/s40508-016-0051-z; (c) C. M. Alder, J. D. Hayler,
R. K. Henderson, A. M. Redman, L. Shukla, L. E. Shuster
and H. F. Sneddon, Green Chem., 2016, 18, 3879–3890;
(d) P. M. Murray, F. Bellany, L. Benhamou, D.-K. Bučar,
A. B. Tabor and T. D. Sheppard, Org. Biomol. Chem., 2016,
14, 2373–2384; (e) C. R. McElroy, A. Constantinou,
L. C. Jones, L. Summerton and J. H. Clark, Green Chem.,
2015, 17, 3111–3121; (f) F. Pena-Pereira, A. Kloskowski and
J. Namieśnik, Green Chem., 2015, 17, 3687–3705;
(g) D. Prat, J. Hayler and A. Wells, Green Chem., 2014, 16,
4546–4551.
9 D. S. Babu, D. Srinivasulu and V. S. Kotakadi, Chem.
Heterocycl. Compd., 2015, 51, 60–66.
10 (a) J. Saadi and H. Wennemers, Nat. Chem., 2016, 8, 276–
280; (b) L. Meazza, J. A. Foster, K. Fucke, P. Metrangolo,
G. Resnati and J. W. Steed, Nat. Chem., 2012, 11, 42–47.
11 (a) Y. Kununobu, H. Ida, M. Nishi and M. Kanai, Nat.
Chem., 2015, 17, 712–717; (b) R. Dalpozzo, Green Chem.,
2015, 17, 3671–3686.
12 (a) D. Kumar, S. R. Vemula and G. R. Cook, Green Chem.,
2015, 17, 4300–4306; (b) A. K. Ghosh and M. Brindisi,
J. Med. Chem., 2015, 58, 2896–2940.
13 M. Liu, L. Liang, X. Li, X. Gao and J. Sun, Green Chem.,
2015, 18, 2851–2863.
14 T. Nishikata, A. R. Abela, S. Huang and B. H. Lipshutz,
J. Am. Chem. Soc., 2010, 132, 4978–4979.
15 (a) G. S. Kumar, R. A. Kumar, P. S. Kumar, N. V. Reddy,
K. V. Kumar, M. L. Kantam, S. Prabhakar and K. R. Reddy,
Chem. Commun., 2013, 49, 6686–6688; (b) H. Lebel and 23 For recent examples of the use of aqueous or alcoholic
O. Leogane, Org. Lett., 2006, 8, 5717–5720; (c) A. Boeijen,
J. van Ameijde and R. M. L. Liskamp, J. Org. Chem., 2001,
66, 8454–8462; (d) S.-H. Lee, H. Matsushita, B. Clapman
and K. D. Janda, Tetrahedron, 2004, 60, 3439–3443;
(e) A. Yagodkin, K. Löschcke, J. Weisell and A. Azhayev,
Tetrahedron, 2010, 66, 2210–2221.
solutions in place of high risk solvents from our laboratory,
see: (a) R. P. Lester, T. Bham, T. W. Bousfield, W. Lewis and
J. E. Camp, J. Org. Chem., 2016, 81, 12472–12477;
(b) S. Kyne and J. E. Camp, ACS Sustainable Chem. Eng.,
2017, 5, 41–48; (c) J. E. Camp, J. J. Dunsford,
O. S. G. Dacosta, R. K. Blundell, J. Adams, J. Britton,
R. J. Smith, T. W. Bousfield and M. W. Fay, RSC Adv., 2016,
6, 16115–16131; (d) M. Rezayat, R. K. Blundell, J. E. Camp,
D. A. Walsh and W. Thielemans, ACS Sustainable Chem.
Eng., 2014, 2, 1241–1250; (e) J. E. Camp, J. J. Dunsford,
E. P. Cannons, W. J. Restorick, A. Gadzhieva, M. W. Fay and
R. J. Smith, ACS Sustainable Chem. Eng., 2014, 2, 500–505;
(f) R. P. Lester and J. E. Camp, ACS Sustainable Chem. Eng.,
2013, 1, 545–548.
16 (a) A. Sarkarm, S. Santra, S. K. Kundu, A. Hajra,
G. V. Zyryanov, O. N. Chupakhin, V. N. Charushin and
A. Majee, Green Chem., 2016, 18, 4475–4525;
(b) A. D. Mamuye, S. Monticelli, L. Castoldi, W. Holzer and
V. Pace, Green Chem., 2015, 17, 4194–4197; (c) C. Ruβ,
F. Ilgen, C. Reil, C. Luff, A. H. Begli and B. König, Green
Chem., 2011, 13, 156–161; (d) C. Wu, H. Cheng, R. Liu,
Q. Wang, Y. Hao, Y. Yu and F. Zhao, Green Chem., 2010, 12,
188–1816; (e) A. Ion, C. Van Doorslaer, V. Parvulescu, 24 J. Sherwood, M. De bruyn, A. Constantinou, L. Moitym,
P. Jacobs and D. De Vos, Green Chem., 2008, 10, 111–116;
(f) B. M. Bhanage, S.-i. Fujita, Y. Ikushima and M. Arai,
Green Chem., 2004, 6, 78–80.
C. R. McElroy, T. J. Farmer, T. Duncan, W. Raverty,
A. J. Hunt and J. H. Clark, Chem. Commun., 2014, 50, 9650–
9652.
17 F. Bigi, R. Maggi and G. Sartori, Green Chem., 2000, 2, 140– 25 For the synthesis of Cyrene from levoglucosenone, see:
148.
G. R. Court, C. H. Lawrence, W. D. Raverty and
18 K. Matsuno, M. Ichimura, T. Nakajima, K. Tahara,
A. J. Duncan, US Pat, 2012/0111714A1, 2012.
S. Fujiwara, H. Kase, J. Ushiki, N. A. Giese, A. Pandey, 26 For the synthesis of levoglucosenone from cellulose, see:
R. M. Scarborough, N. A. Lokker, J.-C. Yu, J. Irie,
E. Tsukuda, S.-i. Ide, S. Oda and Y. Nomoto, J. Med. Chem.,
2002, 45, 3057–3066.
(a) K. Koseki, T. Ebata, H. Kawakami, H. Matsushita,
K. Itoh and Y. Noai, US Pat, 5112994, 1992; (b) F. Cao,
T. J. Schwartz, D. J. McClelland, S. H. Krishna,
J. A. Dumesic and G. W. Huber, Energy Environ. Sci., 2015,
8, 1808–1815.
19 SciFinder search of the reaction of isocyantes and amines
revealed that of 317 934 reactions, 254 600 were run in halo-
This journal is © The Royal Society of Chemistry 2017
Green Chem.