Chemical Science
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3 D. A. Everson, R. Shrestha and D. J. Weix, J. Am. Chem. Soc.,
2010, 132, 920–921.
Kalthoff, F. J. Klauck, M. J. James and F. Glorius, Chem.–
Eur. J., 2018, 24, 17210–17214.
4 Examples of reductive cross couplings with N-
hydroxyphthalimide esters: (a) K. M. Huihui, J. A. Caputo,
Z. Melchor, A. M. Olivares, A. M. Spiewak, K. A. Johnson,
T. A. DiBenedetto, S. Kim, L. K. G. Ackerman and
D. J. Weix, J. Am. Chem. Soc., 2016, 138, 5016–5019; (b)
L. Huang, A. M. Olivares and D. J. Weix, Angew. Chem., Int.
Ed., 2017, 56, 11901–11905; (c) N. Suzuki, J. L. Hofstra,
K. E. Poremba and S. E. Reisman, Org. Lett., 2017, 19,
2150–2153; (d) H. Li, C. P. Breen, H. Seo, T. F. Jamison,
Y.-Q. Fang and M. M. Bio, Org. Lett., 2018, 20, 1338–1341;
(e) X. Lu, X.-X. Wang, T.-J. Gong, J.-J. Pi, S.-J. He and Y. Fu,
Chem. Sci., 2019, 10, 809–814; anhydrides: (f) H. Chen,
L. Hu, W. Ji, L. Yao and X. Liao, ACS Catal., 2018, 8,
10479–10485; benzyl oxalates: (g) X.-B. Yan, C.-L. Li,
W.-J. Jin, P. Guo and X.-Z. Shu, Chem. Sci., 2018, 9, 4529–
4534; tosylates and mesylates: (h) J. H. Liu, C. T. Yang,
X. Y. Lu, Z. Q. Zhang, L. Xu, M. Cui, X. Lu, B. Xiao, Y. Fu
and L. Liu, Chem.–Eur. J., 2014, 20, 15334–15338.
8 J. Hu, G. Wang, S. Li and Z. Shi, Angew. Chem., Int. Ed., 2018,
57, 15227–15231.
9 Examples: (a) M. Leiendecker, C. C. Hsiao, L. Guo,
N. Alandini and M. Rueping, Angew. Chem., Int. Ed., 2014,
53, 12912–12915; (b) L. Guo, A. Chatupheeraphat and
M. Rueping, Angew. Chem., Int. Ed., 2016, 55, 11810–11813;
(c) L. Guo, C.-C. Hsiao, H. Yue, X. Liu and M. Rueping, ACS
Catal., 2016, 6, 4438–4442; (d) L. Guo, X. Liu, C. Baumann
and M. Rueping, Angew. Chem., Int. Ed., 2016, 55, 15415–
15419; (e) X. Liu, C. C. Hsiao, I. Kalvet, M. Leiendecker,
L. Guo, F. Schoenebeck and M. Rueping, Angew. Chem., Int.
Ed., 2016, 55, 6093–6098; (f) H. Yue, L. Guo, S. C. Lee,
X. Liu and M. Rueping, Angew. Chem., Int. Ed., 2017, 56,
3972–3976; (g) H. Yue, L. Guo, H. H. Liao, Y. Cai, C. Zhu
and M. Rueping, Angew. Chem., Int. Ed., 2017, 56, 4282–
4285; (h) H. Yue, C. Zhu and M. Rueping, Angew. Chem.,
Int. Ed., 2018, 57, 1371–1375.
10 F. Chen, K. Chen, Y. Zhang, Y. He, Y.-M. Wang and S. Zhu, J.
Am. Chem. Soc., 2017, 139, 13929–13935.
5 For leading work, see: (a) C. H. Basch, J. Liao, J. Xu, J. J. Piane
and M. P. Watson, J. Am. Chem. Soc., 2017, 139, 5313–5316; 11 (a) Molecular orbital plot, spin density plot, and LOL-p plot
(b) J. Liao, W. Guan, B. P. Boscoe, J. W. Tucker,
J. W. Tomlin, M. R. Garnsey and M. P. Watson, Org. Lett.,
2018, 20, 3030–3033; (c) S. Plunkett, C. H. Basch,
S. O. Santana and M. P. Watson, J. Am. Chem. Soc., 2019,
141, 2257–2262.
were visualized by VMD, see: W. Humphrey, A. Dalke and
K. Schulten, J. Mol. Graphics, 1996, 14, 33–38; (b) Molecular
orbitals, spin density, LOL–p, and multi-center bond order
were analyzed by Multiwfn 3.6. see: T. Lu and F. Chen, J.
Comput. Chem., 2012, 33, 580–592.
6 (a) F. J. Klauck, M. J. James and F. Glorius, Angew. Chem., Int. 12 (a) H. Schmider and A. Becke, J. Mol. Struct.: THEOCHEM,
Ed., 2017, 56, 12336–12339; (b) X. Jiang, M.-M. Zhang,
W. Xiong, L.-Q. Lu and W.-J. Xiao, Angew. Chem., Int. Ed.,
2019, 58, 2402–2406; (c) F. J. Klauck, H. Yoon, M. J. James,
2000, 527, 51–61; (b) V. Tsirelson and A. Stash, Acta
Crystallogr., Sect. B: Struct. Sci., 2002, 58, 780–785; (c)
H. Jacobsen, Can. J. Chem., 2008, 86, 695–702.
M. Lautens and F. Glorius, ACS Catal., 2018, 9, 236–241; (d) 13 (a) M. Giambiagi, M. S. de Giambiagi and K. C. Mundim,
M. Ociepa, J. Turkowska and D. Gryko, ACS Catal., 2018, 8,
11362–11367.
7 (a) J. Wu, L. He, A. Noble and V. K. Aggarwal, J. Am. Chem.
Soc., 2018, 140, 10700–10704; (b) F. Sandfort, F. Strieth-
Struct. Chem., 1990, 1, 423–427; (b) P. Bultinck, R. Ponec
and S. Van Damme, J. Phys. Org. Chem., 2005, 18, 706–718;
(c) E. Matito, Phys. Chem. Chem. Phys., 2016, 18, 11839–
11846.
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