Green Chemistry
Paper
J. E. Camp, J. Org. Chem., 2016, 81, 12472–12477;
(b) S. Kyne and J. E. Camp, ACS Sustainable Chem. Eng.,
(b) A. Lemhoff, J. Sherwood, C. R. McElroy and A. J. Hunt,
Green Chem., 2018, 20, 136–140.
2017, 5, 41–48; (c) J. E. Camp, J. J. Dunsford, 26 H. A. L. Phuong, L. Cseri, G. F. S. Whitehead, A. Garforth,
O. S. G. Dacosta, R. K. Blundell, J. Adams, J. Britton, P. Budd and G. Szekely, RSC Adv., 2017, 7, 53278–53289.
R. J. Smith, T. W. Bousfield and M. W. Fay, RSC Adv., 2016, 27 K. L. Wilson, J. Murray, C. Jamieson and A. J. B. Watson,
6, 16115–16131; (d) M. Rezayat, R. K. Blundell, J. E. Camp, Org. Biomol. Chem., 2018, 16, 2851–2854.
D. A. Walsh and W. Thielemans, ACS Sustainable Chem. 28 F. I. McGonagle, H. F. Sneddon, C. Jamieson and
Eng., 2014, 2, 1241–1250; (e) J. E. Camp, J. J. Dunsford,
A. J. B. Watson, ACS Sustainable Chem. Eng., 2014, 2, 523–
E. P. Cannons, W. J. Restorick, A. Gadzhieva, M. W. Fay and
532.
R. J. Smith, ACS Sustainable Chem. Eng., 2014, 2, 500–505; 29 For recent examples of Mol. E% calculations, see:
(f) R. P. Lester and J. E. Camp, ACS Sustainable Chem. Eng.,
2013, 1, 545–548.
(a) D. Malferrari, N. Armenise, S. Decesari, P. Galletti and
E. Tagiavini, ACS Sustainable Chem. Eng., 2015, 3, 1579–
1588; (b) N. R. Agrawal, S. P. Bahekar, P. B. Sarode,
S. S. Zade and H. S. Chandak, RSC Adv., 2015, 5, 47053–
47059; (c) B. T. Reid and S. M. Reed, Green Chem., 2016, 18,
4263–4269; (d) M. K. Manish, G. D. Madhunkar and
M. G. Jayant, Solvent-Free Synthesis of Thiobarbituric Acids
Using Amberlyst-15 as a Green Catalyst, Curr. Green Chem.,
2017, 4, 50–56; (e) J. E. Camp, T. W. Bousfield,
J. J. Dunsford, J. Adams, J. Britton, M. W. Fay and
A. Angelis-Dimakis, Synthesis, 2018, 50, 3862–3874.
15 For other potential green replacements for traditional
aprotic dipolar solvents, see: (a) H. L. Parker, J. Sherwood,
A. J. Hunt and J. H. Clark, ACS Sustainable Chem. Eng.,
2014, 2, 1739–1742; (b) D. Rasina, A. Kahler-Quesada,
S. Ziarelli, S. Waratz, H. Cao, S. Santoro, L. Ackermann and
L. Vaccaro, Green Chem., 2016, 18, 5025–5030;
(c) K. L. Wilson, J. Murray, H. F. Sneddon, C. Jamieson and
A. J. B. Watson, Synlett, 2018, 2293–2297.
16 For a review, see: J. E. Camp, ChemSusChem, 2018, 11,
3048–3055.
30 See the ESI† for full details.
17 J. Sherwood, M. De bruyn, A. Constantinou, L. Moity, 31 F. Shafizadeh and P. P. S. Chin, Carbohydr. Res., 1977, 58,
C. R. McElroy, T. J. Farmer, T. Duncan, W. Raverty, A. J. Hunt
and J. H. Clark, Chem. Commun., 2014, 50, 9650–9652.
18 (a) H. J. Salavagione, J. Sherwood, M. De bruyn,
79–87.
32 S. H. Krishna, T. W. Walker, J. A. Dumesic and
G. W. Huber, ChemSusChem, 2017, 10, 129–138.
V. L. Budarin, G. J. Ellis, J. H. Clark and P. S. Shuttleworth, 33 A. V. Samet, M. E. Niyazymbetov and V. V. Semenov, J. Org.
Green Chem., 2017, 19, 2550–2560; (b) D. H. Gharib, Chem., 1996, 61, 8786–8791.
S. Gietman, F. Malherbe and S. E. Moulton, Carbon, 2017, 34 M. De bruyn, V. L. Budarin, A. Misefari, S. Shimizu,
123, 695–707.
H. Fish, M. Cockett, A. J. Hunt, H. Hofstetter,
B. M. Weckhuysen, J. H. Clark and D. J. Macquarrie, ACS
Sustainable Chem. Eng., 2019, 7, 7878–7883.
19 J. Zhang, G. B. White, M. D. Ryan, A. J. Hunt and
M. J. Katz, ACS Sustainable Chem. Eng., 2016, 4, 7186–7192.
20 T. Marino, F. Galiano, A. Molino and A. Figoli, J. Membr. 35 (a) Y. Chiang, A. J. Kresge, Y. S. Tang and J. Wirz, J. Am.
Sci., 2019, 580, 224–234.
21 (a) S. Lawrenson, M. North, F. Peigneguy and A. Routledge,
Chem. Soc., 1984, 106, 460–463; (b) T. Shikata and
M. Okuzono, J. Phys. Chem. B, 2013, 117, 7718–7723.
Green Chem., 2017, 19, 952–962; (b) Y. Ran, F. Byrne, 36 C. Jiménez-González, C. S. Ponder, Q. Broxterman and
I. Ingram and M. North, Chem. – Eur. J., 2019, 25, 4951–
4964.
22 L. Mistry, K. Mapesa, T. W. Bousfield and J. E. Camp, Green
Chem., 2017, 19, 2123–2128.
J. Manley, Org. Process Res. Dev., 2011, 15, 912–917.
37 H. Kurouchi, K. Kawamoto, H. Sugimoto, S. Nakamura,
Y. Otani and T. Ohwada, J. Org. Chem., 2012, 77, 9313–
9328.
23 K. L. Wilson, A. R. Kennedy, J. Murray, B. Greatrex, 38 B. D. Lee, Z. Li, K. J. French, Y. Zhuang, Z. Xia and
C. Jamieson and A. J. B. Watson, Beilstein J. Org. Chem.,
2016, 12, 2005–2011.
24 K. L. Wilson, J. Murray, C. Jamieson and A. J. B. Watson,
Synlett, 2018, 29, 650–654.
C. D. Smith, J. Med. Chem., 2004, 47, 1413–1422.
39 M. D. Reddy, A. N. Blanton and E. B. Watkins, J. Org.
Chem., 2017, 82, 5080–5095.
40 W. Li and X.-F. Wu, J. Org. Chem., 2014, 79, 10410–10416.
25 (a) A. G. Lanctôt, T. M. Attard, J. Sherwood, C. R. McElroy 41 M. Konishi, K. Tsuchida, K. Sano, T. Kochi and
and A. J. Hunt, RSC Adv., 2016, 6, 48753–48756;
F. Kakiuchi, J. Org. Chem., 2017, 82, 8716–8724.
This journal is © The Royal Society of Chemistry 2019
Green Chem.