Chemical Science
Edge Article
Horizon 2020 research and innovation programme (grant
agreement no. 741623). We thank Dr Rudolf Vasold for GC-MS
measurements, Regina Hoheisel for cyclic voltammetry
measurements and Willibald Stockerl for NMR measurements.
R. Martin, Angew. Chem., Int. Ed., 2017, 56, 10915–10919;
(d) W. Kong, H. An and Q. Song, Chem. Commun., 2017, 53,
8968–8971; (e) J. P. Phelan, S. B. Lang, J. S. Compton,
C. B. Kelly, R. Dykstra, O. Gutierrez and G. A. Molander, J.
Am. Chem. Soc., 2018, 140, 8037–8047; (f) C. Shu,
R. S. Mega, B. J. Andreassen, A. Noble and V. K. Aggarwal,
Angew. Chem., Int. Ed., 2018, 57, 15430–15434; (g)
K. Donabauer, M. Maity, A. L. Berger, G. S. Huff, S. Crespi
Notes and references
1 (a) J. B. Hendrickson, J. Am. Chem. Soc., 1975, 97, 5784–5800;
(b) J. C. Lewis, P. S. Coelho and F. H. Arnold, Chem. Soc. Rev.,
2011, 40, 2003–2021.
2 (a) J. Yamaguchi, A. D. Yamaguchi and K. Itami, Angew.
Chem., Int. Ed., 2012, 51, 8960–9009; (b) L. McMurray,
F. O'Hara and M. J. Gaunt, Chem. Soc. Rev., 2011, 40, 1885–
1898.
3 (a) T. B. Poulsen and K. A. Jorgensen, Chem. Rev., 2008, 108,
2903–2915; (b) F. Denes, A. Perez-Luna and F. Chemla, Chem.
Rev., 2010, 110, 2366–2447; (c) J. He, M. Wasa, K. S. L. Chan,
Q. Shao and J. Q. Yu, Chem. Rev., 2017, 117, 8754–8786; (d)
Y. Yang, J. Lan and J. You, Chem. Rev., 2017, 117, 8787–
8863; (e) Z. Dong, Z. Ren, S. J. Thompson, Y. Xu and
G. Dong, Chem. Rev., 2017, 117, 9333–9403; (f) H. M. Davies
and D. Morton, Chem. Soc. Rev., 2011, 40, 1857–1869; (g)
H. Yi, G. Zhang, H. Wang, Z. Huang, J. Wang, A. K. Singh
and A. Lei, Chem. Rev., 2017, 117, 9016–9085; (h) T. Cernak,
K. D. Dykstra, S. Tyagarajan, P. Vachal and S. W. Krska,
Chem. Soc. Rev., 2016, 45, 546–576.
¨
and B. Konig, Chem. Sci., 2019, 10, 5162–5166; (h) L. Pitzer,
J. L. Schwarz and F. Glorius, Chem. Sci., 2019, 10, 8285–8291.
9 (a) V. Grignard, C. R. Acad. Sci., Ser. Gen. Vie Sci., 1900, 130,
1322–1325; (b) C.-J. Li, Tetrahedron, 1996, 52, 5643–5668; (c)
G. S. Silverman and P. E. Rakita, Handbook of Grignard
Reagents, Marcel Dekker, Inc., New York, 1996; (d)
P. Barbier, C. R. Acad. Sci., Ser. Gen. Vie Sci., 1899, 128,
110–111.
10 S. Ni, N. M. Padial, C. Kingston, J. C. Vantourout,
D. C. Schmitt, J. T. Edwards, M. M. Kruszyk,
R. R. Merchant, P. K. Mykhailiuk, B. B. Sanchez, S. Yang,
M. A. Perry, G. M. Gallego, J. J. Mousseau, M. R. Collins,
R. J. Cherney, P. S. Lebed, J. S. Chen, T. Qin and
P. S. Baran, J. Am. Chem. Soc., 2019, 141, 6726–6739.
11 F. G. Bordwell, D. Algrim and N. R. Vanier, J. Org. Chem.,
1977, 42, 1817–1819.
12 K. Chatterjee, M. Miyake and L. M. Stock, Energy Fuels, 1990,
4, 242–248.
4 W. Liu, Z. Ren, A. T. Bosse, K. Liao, E. L. Goldstein, J. Bacsa,
D. G. Musaev, B. M. Stoltz and H. M. L. Davies, J. Am. Chem.
Soc., 2018, 140, 12247–12255.
13 F. G. Bordwell, Acc. Chem. Res., 2002, 21, 456–463.
14 Q. Y. Meng, T. E. Schirmer, A. L. Berger, K. Donabauer and
¨
B. Konig, J. Am. Chem. Soc., 2019, 141, 11393–11397.
5 (a) S. Protti, M. Fagnoni and D. Ravelli, ChemCatChem, 2015,
7, 1516–1523; (b) L. Capaldo and D. Ravelli, Eur. J. Org.
Chem., 2017, 2017, 2056–2071.
6 (a) D. Hager and D. W. MacMillan, J. Am. Chem. Soc., 2014,
136, 16986–16989; (b) J. C. Chu and T. Rovis, Nature, 2016,
539, 272–275; (c) A. Hu, J. J. Guo, H. Pan, H. Tang, Z. Gao
and Z. Zuo, J. Am. Chem. Soc., 2018, 140, 1612–1616; (d)
M. D. Vu, M. Das, A. X. Guo, Z. E. Ang, M. Dokic, H. S. Soo
and X. W. Liu, ACS Catal., 2019, 9, 9009–9014.
7 (a) Y. Zhang, R. Qian, X. Zheng, Y. Zeng, J. Sun, Y. Chen,
A. Ding and H. Guo, Chem. Commun., 2015, 51, 54–57; (b)
D. Ravelli, S. Protti and M. Fagnoni, Chem. Rev., 2016, 116,
9850–9913.
15 J. D. Cuthbertson and D. W. MacMillan, Nature, 2015, 519,
74–77.
16 (a) A. Banerjee, Z. Lei and M. Y. Ngai, Synthesis, 2019, 51,
303–333; (b) K. Yoshikai, T. Hayama, K. Nishimura,
K. Yamada and K. Tomioka, J. Org. Chem., 2005, 70, 681–
683; (c) B. P. Roberts, Chem. Soc. Rev., 1999, 28, 25–35.
17 C. Le, Y. Liang, R. W. Evans, X. Li and D. W. C. MacMillan,
Nature, 2017, 547, 79–83.
18 H. Tanaka, K. Sakai, A. Kawamura, K. Oisaki and M. Kanai,
Chem. Commun., 2018, 54, 3215–3218.
19 J. A. Murphy, S. Z. Zhou, D. W. Thomson, F. Schoenebeck,
M. Mahesh, S. R. Park, T. Tuttle and L. E. Berlouis, Angew.
Chem., Int. Ed., 2007, 46, 5178–5183.
8 (a) L. L. Liao, G. M. Cao, J. H. Ye, G. Q. Sun, W. J. Zhou,
Y. Y. Gui, S. S. Yan, G. Shen and D. G. Yu, J. Am. Chem.
Soc., 2018, 140, 17338–17342; (b) Y. Kumagai, T. Naoe,
K. Nishikawa, K. Osaka, T. Morita and Y. Yoshimi, Aust. J.
Chem., 2015, 68, 1668; (c) V. R. Yatham, Y. Shen and
20 E. Speckmeier, T. G. Fischer and K. Zeitler, J. Am. Chem. Soc.,
2018, 140, 15353–15365.
21 D. D. M. Wayner, D. J. McPhee and D. Griller, J. Am. Chem.
Soc., 1988, 110, 132–137.
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