Green Chemistry
Paper
2 Selected reviews: (a) A. D. Sonawane and M. Koketsu, Curr.
Org. Chem., 2019, 23, 3206; (b) I. P. Beletskaya and
V. P. Ananikov, Chem. Rev., 2011, 111, 1596;
(c) N. Petragnani, H. A. Stefani and C. J. Valduga,
Tetrahedron, 2001, 57, 1411; (d) F. V. Singh and T. Wirth,
Encyclopedia of Inorganic and Bioinorganic Chemistry, 2018, 1.
D. Xu, D. Xie, H. Guo and W. Wang, J. Org. Chem., 2005, 70,
5678; (c) I. Ryu, S. Murai, I. Niwa and N. Sonoda, Synthesis,
1977, 874; (d) H. J. Reich, I. L. Reich and J. M. Renga, J. Am.
Chem. Soc., 1973, 95, 5813; (e) J. Cossy and N. Furet,
Tetrahedron Lett., 1993, 34, 7755; (f) M. Nazari and
B. Movassagh, Tetrahedron Lett., 2009, 50, 1453.
3 Selected examples: (a) H. J. Reich, J. M. Renga and 14 Selected references: (a) I. Beletskaya, A. Sigeev,
I. L. Reich, J. Am. Chem. Soc., 1975, 97, 5434;
(b) K. B. Sharpless, R. F. Lauer and A. Y. Teranishi, J. Am.
Chem. Soc., 1973, 95, 6137.
4 Selected examples: (a) P. Lerouge and C. Paulmier,
Tetrahedron Lett., 1984, 25, 1987; (b) P. Lerouge and
C. Paulmier, Bull. Soc. Chim. Fr., 1985, 1225.
A. Peregudov and P. Petrovskii, Chem. Lett., 2005, 34, 1348;
(b) T. Ying, W. Bao and Y. Zhang, Synth. Commun., 1996,
26, 1517; (c) Y. Nishiyama, H. Kawamatsu, S. Funato,
K. Tokunaga and N. Sonoda, J. Org. Chem., 2003, 68, 3599;
(d) W. L. Bao and Y. M. Zhang, Synlett, 1996, 1187;
(e) S. V. Ley, L. A. O’Neil and C. M. R. Low, Tetrahedron,
1986, 42, 5363.
5 Selected examples: (a) J. N. Fitzner, R. G. Shea,
J. E. Fankhauser and P. B. Hopkins, J. Org. Chem., 1985, 50, 15 Selected references: (a) M. Shimizu and I. Kuwajima, Bull.
417; (b) R. G. Shea, J. N. Fitzner, J. E. Fankhauser,
A. Spaltenstein, P. A. Carpino, R. M. Peevey, D. V. Pratt,
B. J. Tenge and P. B. Hopkins, J. Org. Chem., 1986, 51, 5243;
Chem. Soc. Jpn., 1981, 54, 3100; (b) I. Kuwajima and
M. Shimizu, Tetrahedron Lett., 1978, 1277; (c) M. Shimizu,
R. Takeda and I. Kuwajima, Tetrahedron Lett., 1979, 419.
(c) A. Spaltenstein, P. A. Carpino and P. B. Hopkins, 16 R. Senatore, L. Castoldi, L. Ielo, W. Holzer and V. Pace, Org.
Tetrahedron Lett., 1986, 27, 147. Lett., 2018, 20, 2685.
6 Selected examples: (a) I. Ryu, H. Muraoka, N. Kambe, 17 J. Schwartz and Y. Hayasi, Tetrahedron Lett., 1980, 21, 1497.
M. Komatsu and N. Sonoda, J. Org. Chem., 1996, 61, 6396; 18 (a) D. Houllemare, S. Ponthieux, F. Outurquin and
(b) M. Besev and L. Engman, Org. Lett., 2000, 2, 1589.
7 Selected reviews: (a) S. T. Manjare, Y. Kim and
D. G. Churchill, Acc. Chem. Res., 2014, 47, 2985;
C. Paulmier, Synthesis, 1997, 101; (b) B. Movassagh and
A. Yousefi, Monatsh. Chem., 2014, 145, 1173; (c) R. Chen,
W. Su and W. Zhong, J. Chem. Res., 2005, 620.
(b) S. A. Akhoon, T. Naqvi, S. Nisar and M. A. Rizvi, Asian J. 19 (a) T. Newhouse, P. S. Baran and R. W. Hoffmann, Chem.
Chem., 2015, 27, 2745; (c) Q. Miao, J. Xu, A. Lin, X. Wu,
L. Wu and W. Xie, Curr. Med. Chem., 2018, 25, 2009.
Soc. Rev., 2009, 38, 3010; (b) P. J. Dunn, Chem. Soc. Rev.,
2012, 41, 1452; (c) R. A. Sheldon, Green Chem., 2017, 19, 18.
8 Selected references: (a) M. F. B. Gerzson, F. N. Victoria, 20 Selected reviews: (a) K. L. Skubi, T. R. Blum and T. P. Yoon,
C. S. Radatz, M. G. de Gomes, S. P. Boeira, R. G. Jacob,
D. Alves, C. R. Jesse and L. Savegnago, Pharmacol., Biochem.
Behav., 2012, 102, 21; (b) F. S. S. Sousa, P. T. Birmann,
R. Baldinotti, M. G. Fronza, R. Balaguez, D. Alves,
C. A. Bruning and L. Savegnago, Brain Res. Bull., 2018, 142,
129.
Chem. Rev., 2016, 116, 10035; (b) D. Ravelli, S. Protti and
M. Fagnoni, Chem. Rev., 2016, 116, 9850; (c) M. H. Shaw,
J. Twilton and D. W. C. MacMillan, J. Org. Chem., 2016, 81,
6898; (d) I. K. Sideri, E. Voutyritsa and C. G. Kokotos, Org.
Biomol. Chem., 2018, 16, 4596; (e) M. A. Theodoropoulou,
N. F. Nikitas and C. G. Kokotos, Beilstein J. Org. Chem.,
2020, 16, 833.
9 Selected references: (a) J. Hu, L. Engman and
I. A. Cotgreave, Carcinogenesis, 1995, 16, 1815; 21 (a) T. Punniyamurthy, S. Velusamy and J. Iqbal, Chem. Rev.,
(b) K. M. Nikolic, QSAR Comb. Sci., 2007, 26, 358.
10 L. Engman, I. Cotgreave, M. Angulo, C. W. Taylor,
G. D. Paine-Murrieta and G. Powis, Anticancer Res., 1997,
17, 4599.
2005, 105, 2329; (b) Y.-F. Liang and N. Jiao, Acc. Chem. Res.,
2017, 50, 1640; (c) A. A. Ghogare and A. Greer, Chem. Rev.,
2016, 116, 9994; (d) N. F. Nikitas, D. I. Tzaras,
I. Triandafillidi and C. G. Kokotos, Green Chem., 2020, 22,
471.
11 Selected references: (a) I. A. Cotgreave, P. Moldeus,
R. Brattsand, A. Hallberg, C. M. Andersson and L. Engman, 22 (a) W. Yi, P.-F. Wang, M. Lu, Q.-Q. Liu, X. Bai, K.-D. Chen,
Biochem. Pharmacol., 1992, 43, 793; (b) F. Martínez-Ramos,
H. Salgado-Zamora, M. E. Campos-Aldrete, E. Melendez-
Camargo, Y. Márquez-Flores and M. Soriano-García,
Eur. J. Med. Chem., 2008, 43, 1432.
J.-W. Zhang and G.-Q. Liu, ACS Sustainable Chem. Eng.,
2019, 7, 16777; (b) X.-X. Fang, P.-F. Wang, W. Yi, W. Chen,
S.-C. Lou and G.-Q. Liu, J. Org. Chem., 2019, 84, 15677;
(c) W. Yi, Q.-Y. Liu, X.-X. Fang, S.-C. Lou and G.-Q. Liu, Org.
Biomol. Chem., 2018, 16, 7012; (d) W. Yi, X.-X. Fang,
Q.-Y. Liu and G.-Q. Liu, Eur. J. Org. Chem., 2018, 6671;
(e) J. Liu, Q.-Y. Liu, X.-X. Fang, G.-Q. Liu and Y. Ling, Org.
Biomol. Chem., 2018, 16, 7454.
12 Selected references: (a) L. Engman, C. Andersson,
R. Morgenstern, I. A. Cotgreave, C. M. Andersson and
A. Hallberg, Tetrahedron, 1994, 50, 2929; (b) L. Engman,
A. Tunek, M. Hallberg and A. Hallberg, Chem.-Biol.
Interact., 1994, 93, 129; (c) K. J. Szabo, H. Frisell, 23 (a) U. Schmidt, A. Mueller and K. Markau, Chem. Ber.,
L. Engman, M. Piatek, B. Oleksyn and J. Sliwinski, J. Mol.
Struct., 1998, 448, 21.
1964, 97, 405; (b) A. Ogawa, R. Obayashi, M. Doi, N. Sonoda
and T. Hirao, J. Org. Chem., 1998, 63, 4277.
13 Selected references: (a) W. Wang, J. Wang and H. Li, Org. 24 (a) O. Ito, J. Am. Chem. Soc., 1983, 105, 850; (b) T. G. Back
Lett., 2004, 6, 2817; (b) J. Wang, H. Li, Y. Mei, B. Lou,
and M. V. Krishna, J. Org. Chem., 1988, 53, 2533.
This journal is © The Royal Society of Chemistry 2021
Green Chem., 2021, 23, 1840–1846 | 1845