Paper
Green Chemistry
D. J. Procter, Chem. Soc. Rev., 2019, 48, 4626;
(b) K. C. Nicolaou and J. S. Chen, Chem. Soc. Rev., 2009, 38,
C.-L. Zhu, Z.-X. Jia and H. Xu, J. Am. Chem. Soc., 2014, 136,
13186.
2993; (c) J. M. Sperl and V. Sieber, ACS Catal., 2018, 8, 2385; 12 For recent reviews on the Chan–Lam reaction, see:
(d) G. Zhang, Y. Liu, J. Zhao, Y. Li and Q. Zhang, Sci. China:
Chem., 2019, 62, 1476; (e) L.-Q. Lu, J.-R. Chen and
W.-J. Xiao, Acc. Chem. Res., 2012, 45, 1278.
2 The principles of green and sustainable chemistry:
(a) R. A. Sheldon, Chem. Soc. Rev., 2012, 41, 1437;
(b) R. A. Sheldon, Green Chem., 2007, 9, 1273.
(a) J. X. Qiao and P. Y. S. Lam, Synthesis, 2011, 6, 829;
(b) K. S. Rao and T.-S. Wu, Tetrahedron, 2012, 68, 7735;
(c) P. Y. S. Lam, Handbook of “Synthetic methods in drug dis-
covery”, RSC, 2016, ch. 7, vol. 1, p. 242; (d) X.-P. Ma,
F.-P. Liu and D.-L. Mo, Chin. J. Org. Chem., 2017, 37, 1069;
(e) L. Lei, C.-J. Li and D.-L. Mo, Chin. J. Org. Chem., 2019,
39, 2989.
3 (a) J. W. B. Fyfe and A. J. B. Watson, Chem, 2017, 3, 31;
(b) A. J. J. Lennox and G. C. Lloyd-Jones, Chem. Soc. Rev., 13 For examples of the N–O bond coupling reaction in our
2014, 43, 412; (c) X. Yang, S. J. Kalita, S. Maheshuni
and Y.-Y. Huang, Coord. Chem. Rev., 2019, 392, 35;
(d) D. G. Hall, Boronic Acids: Preparation and Applications in
Organic Synthesis Medicine and Materials, Wiley-VCH,
New York, 2011.
group, see: (a) W.-M. Shi, F.-P. Liu, Z.-X. Wang, H.-Y. Bi,
C. Liang, L.-P. Xu, G.-F. Su and D.-L. Mo, Adv. Synth. Catal.,
2017, 359, 2741; (b) C.-H. Chen, Q.-Q. Liu, X.-P. Ma,
Y. Feng, C. Liang, C.-X. Pan, G.-F. Su and D.-L. Mo, J. Org.
Chem., 2017, 82, 6417.
4 For examples of alkenylboron reagents in the coupling reac- 14 For examples of N–O bond rearrangement, see: (a) N. Zou,
tion, see: (a) R. E. Shade, A. M. Hyde, J.-C. Olsen and
C. A. Merlic, J. Am. Chem. Soc., 2010, 132, 1202;
(b) D. G. Chan, D. J. Winternherimer and C. A. Merlic, Org.
Lett., 2011, 13, 2778; (c) J. Ohata, M. B. Minus,
M. E. Abernathy and Z. T. Ball, J. Am. Chem. Soc., 2016, 138,
7472; (d) F. Huang, T. D. Quach and R. A. Batey, Org. Lett.,
2013, 15, 3150; (e) D.-L. Mo, D. A. Wink and L. L. Anderson,
Org. Lett., 2012, 14, 5180; (f) J. Son, K. H. Kim, D.-L. Mo,
D. J. Wink and L. L. Anderson, Angew. Chem., Int. Ed., 2017,
J.-W. Jiao, Y. Feng, C.-X. Pan, C. Liang, G.-F. Su and
D.-L. Mo, Org. Lett., 2019, 21, 481; (b) S.-Y. Wu, W.-L. Chen,
X.-P. Ma, C. Liang, G.-F. Su and D.-L. Mo, Adv. Synth. Catal.,
2019, 361, 965; (c) C.-H. Chen, Q.-Y. Wu, C. Wei, C. Liang,
G.-F. Su and D.-L. Mo, Green Chem., 2018, 20, 2722;
(d) X.-P. Ma, L.-G. Li, H.-P. Zhao, M. Du, C. Liang and
D.-L. Mo, Org. Lett., 2018, 20, 4571; (e) J.-Y. Liao, Q.-Y. Wu,
X. Lu, N. Zou, C.-X. Pan, C. Liang, G.-F. Su and D.-L. Mo,
Green Chem., 2019, 21, 6567.
56, 3059; (g) T. W. Reidl, J. Son, D. J. Wink and 15 For examples of condensations, see: (a) K. Haav,
L. L. Anderson, Angew. Chem., Int. Ed., 2017, 56, 11579;
(h) H.-Y. Wang and L. L. Anderson, Org. Lett., 2013, 15,
3362.
5 For recent reviews, see: (a) J.-S. Zhang, L. Liu, T. Chen and
L.-B. Han, Chem. – Asian J., 2018, 13, 2277; (b) N. Kaur,
F. Wu, N.-E. Alom, J. P. Ariyarathna, S. J. Saluga and W. Li,
Org. Biomol. Chem., 2019, 17, 1643.
6 For selected examples of difunctionalization of alkenyl-
boron reagents, see: (a) R. N. Khanizeman, E. Barde,
R. W. Bates, A. Guérinot and J. Cossy, Org. Lett., 2017, 19,
5046; (b) J.-W. Jiao, H.-Y. Bi, P.-S. Zou, Z.-X. Wang, C. Liang
and D.-L. Mo, Adv. Synth. Catal., 2018, 360, 3254.
7 A. S. Patil, D.-L. Mo, H.-Y. Wang, D. S. Mueller and
L. L. Anderson, Angew. Chem., Int. Ed., 2012, 51, 7799.
8 W.-X. Lv, Y.-F. Zeng, Q. Li, Y. Chen, D.-H. Tan, L. Yang and
H. Wang, Angew. Chem., Int. Ed., 2016, 55, 10069.
9 (a) H.-S. Yeom and S. Shin, Acc. Chem. Res., 2014, 47, 966;
(b) X.-G. Liu, H. Gao, S.-S. Zhang, Q. Li and H. Wang, ACS
Catal., 2017, 7, 5078.
S. A. Kadam, L. Toom, P. A. Gale, N. Busschaert,
˜
M. Wenzel, J. R. Hiscock, I. L. Kirby, T. Haljasorg, M. Lokov
and I. Leito, J. Org. Chem., 2013, 78, 7796; (b) S. Kotha,
M. Saifuddin and V. R. Aswar, Org. Biomol. Chem., 2016, 14,
9868; (c) D. Curiel, A. Cowley and P. D. Beer, Chem.
Commun., 2005, 236.
16 For examples of the Japp–Klingermann reaction, see:
(a) M. D. Meyer and L. I. Kruse, J. Org. Chem., 1984, 49,
3195; (b) D. P. Chakraborty and B. K. Chowdhury, J. Org.
Chem., 1968, 33, 1265; (c) D. P. Charkraborty, A. Islam and
P. Bhattacharyya, J. Org. Chem., 1973, 38, 2728.
17 (a) C.-F. Kuok, J. Zhang, C.-L. Fan, Q.-W. Zhang, R.-Z. Fan,
D.-M. Zhang, X.-Q. Zhang and W.-C. Ye, Tetrahedron Lett.,
2017, 58, 2740; (b) J. A. Joule, M. Ohashi, B. Gilbert and
C. Djerassi, Tetrahedron, 1965, 21, 1717; (c) H.-J. Knölker
and K. R. Reddy, Chem. Rev., 2001, 102, 4303; (d) J. Guo,
I. N. C. Kiran, R. S. Reddy, J. Gao, M. Tang, Y. Liu and
Y. He, Org. Lett., 2016, 18, 2499; (e) J. T. Kuethe, A. Wong
and I. W. Davies, Org. Lett., 2003, 5, 3721.
10 For C–H amination, see: (a) J. Shi, G. Zhao, X. Wang, 18 For selected recent examples of preparation of indole and
H. E. Xu and W. Yi, Org. Biomol. Chem., 2014, 12, 6831;
(b) L.-L. Xu, X. Wang, B. Ma, M.-X. Yin, H.-X. Lin, H.-X. Dai
and J.-Q. Yu, Chem. Sci., 2018, 9, 5160; (c) M. Zou, J. Liu,
C. Tang and N. Jiao, Org. Lett., 2016, 18, 3030.
carbazole scaffolds, see: (a) B.-Q. Gu, W.-L. Yang, S.-X. Wu,
Y.-B. Wang and W.-P. Deng, Org. Chem. Front., 2018, 5,
3430; (b) G.-J. Mei and F. Shi, Chem. Commun., 2018, 54,
6607; (c) C. Zheng and S.-L. You, Nat. Prod. Rep., 2019, 36,
1589; (d) Y. Wang, P. Zhang, Y. Liu, F. Xia and J. Zhang,
Chem. Sci., 2015, 6, 5564; (e) J. Dong, D. Zhang, Y. Men,
X. Zhang, Z. Hu and X. Xu, Org. Lett., 2019, 21, 166;
(f) H.-P. Zhao, G.-C. Liang, S.-M. Nie, X. Lu, C.-X. Pan,
X.-X. Zhong, G.-F. Su and D.-L. Mo, Green Chem., 2020, 22, 404.
11 (a) A.-D. Manick, S. Aubert, B. Yalcouye, T. Prange,
F. Berhal and G. Prestat, Chem. – Eur. J., 2018, 24, 11485;
(b) D. J. Michaelis, C. J. Shaffer and T. P. Yoon, J. Am. Chem.
Soc., 2007, 129, 1866; (c) B. N. Hemric, A. W. Chen and
Q. Wang, J. Org. Chem., 2019, 84, 1468; (d) D.-F. Lu,
Green Chem.
This journal is © The Royal Society of Chemistry 2020