Organic Letters
Experimental details and full spectroscopic data for all
Letter
Sato, R.; Annamalai, P.; Chuang, S.-C.; Cheng, C.-H. Green Chem.
2017, 19, 3219.
(6) (a) Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem., Int.
Ed. 2011, 50, 6379. (b) Deponti, M.; Kozhushkov, S. I.; Yufit, D. S.;
Ackermann, L. Org. Biomol. Chem. 2013, 11, 142. (c) Yedage, S. L.;
Bhanage, B. M. Green Chem. 2016, 18, 5635.
(7) (a) Grigorjeva, L.; Daugulis, O. Angew. Chem., Int. Ed. 2014, 53,
10209. (b) Zhai, S.; Qiu, S.; Chen, X.; Wu, J.; Zhao, H.; Tao, C.; Li,
Y.; Cheng, B.; Wang, H.; Zhai, H. Chem. Commun. 2018, 54, 98.
(c) Mei, R.; Sauermann, N.; Oliveira, J. C. A.; Ackermann, L. J. Am.
Chem. Soc. 2018, 140, 7913. (d) Tang, S.; Wang, D.; Liu, Y.; Zeng, L.;
Lei, A. Nat. Commun. 2018, 9, 798.
(8) (a) Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N. J.
Am. Chem. Soc. 2011, 133, 14952. (b) Wang, H.; Glorius, F. Angew.
Chem., Int. Ed. 2012, 51, 7318. (c) Obata, A.; Ano, Y.; Chatani, N.
Chem. Sci. 2017, 8, 6650. (d) Xu, G. D.; Huang, Z. Z. Org. Lett. 2017,
19, 6265.
AUTHOR INFORMATION
Corresponding Authors
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ORCID
Notes
The authors declare no competing financial interest.
(9) (a) Shu, Z.; Li, W.; Wang, B. ChemCatChem 2015, 7, 605.
(b) Shu, Z.; Guo, Y.; Li, W.; Wang, B. Catal. Today 2017, 297, 292.
(10) (a) Cera, G.; Haven, T.; Ackermann, L. Chem. Commun. 2017,
53, 6460. (b) Mo, J.; Muller, T.; Oliveira, J. C. A.; Ackermann, L.
Angew. Chem., Int. Ed. 2018, 57, 7719.
ACKNOWLEDGMENTS
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We thank the National Natural Science Foundation of China
(Nos. 21871187 and 21572137), the Key Program of Sichuan
Science, Technology Project (No. 2019YFG0146), and the
Research Fund of Department of Education of Sichuan
Province (No. 18ZB0481) for financial support. We also
thank the comprehensive training platform of specialized
laboratory, College of Chemistry, and Chunchun Zhang from
the Centre of Testing & Analysis, Sichuan University, for
NMR measurements.
(11) Phatake, R. S.; Patel, P.; Ramana, C. V. Org. Lett. 2016, 18,
2828.
(12) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407.
(13) (a) Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem.
2009, 74, 6295. (b) Ackermann, L.; Pospech, J. Org. Lett. 2011, 13,
4153. (c) Bechtoldt, A.; Tirler, C.; Raghuvanshi, K.; Warratz, S.;
Kornhaass, C.; Ackermann, L. Angew. Chem., Int. Ed. 2016, 55, 264−7.
(d) Zhu, Y.-Q.; Li, J.-X.; Han, T.-F.; He, J.-L.; Zhu, K. Eur. J. Org.
Chem. 2017, 2017, 806. (e) Bechtoldt, A.; Baumert, M. E.; Vaccaro,
L.; Ackermann, L. Green Chem. 2018, 20, 398. (f) Qiu, Y.; Kong, W.
J.; Struwe, J.; Sauermann, N.; Rogge, T.; Scheremetjew, A.;
Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5828.
(14) Nandi, D.; Ghosh, D.; Chen, S. J.; Kuo, B. C.; Wang, N. M.;
Lee, H. M. J. Org. Chem. 2013, 78, 3445.
(15) Zhang, M.; Zhang, H. J.; Han, T.; Ruan, W.; Wen, T. B. J. Org.
Chem. 2015, 80, 620.
(16) Nguyen, T. T.; Grigorjeva, L.; Daugulis, O. Angew. Chem., Int.
Ed. 2018, 57, 1688.
(17) (a) Stach, M.; Lacík, I.; Kasak, P.; Chorvat, D. a.; Saunders, A.
J.; Santanakrishnan, S.; Hutchinson, R. A. Macromol. Chem. Phys.
2010, 211, 580. (b) Chen, Y.; Ho, W. S. W. J. Membr. Sci. 2016, 514,
376.
(18) (a) Frasco, D. A.; Lilly, C. P.; Boyle, P. D.; Ison, E. A. ACS
Catal. 2013, 3, 2421. (b) Zhou, J.; Shi, J.; Qi, Z.; Li, X.; Xu, H. E.; Yi,
W. ACS Catal. 2015, 5, 6999. (c) Erbing, E.; Sanz-Marco, A.;
REFERENCES
■
(1) (a) Agata, N.; Nogi, H.; Milhollen, M.; Kharbanda, S.; Kufe, D.
Cancer Res. 2004, 64, 8512. (b) Sloman, D. L.; Bacon, J. W.; Porco, J.
A. J. Am. Chem. Soc. 2011, 133, 9952. (c) Wei, L.; Xue, J.; Liu, H.;
Wang, W.; Li, Y. Org. Lett. 2012, 14, 5302. (d) Jin, Z. Nat. Prod. Rep.
2013, 30, 849. (e) Wilsdorf, M.; Reissig, H. U. Angew. Chem., Int. Ed.
2014, 53, 4332.
(2) (a) Lewis, J. R. Nat. Prod. Rep. 1993, 10, 291. (b) Brookings, D.;
Davenport, R. J.; Davis, J.; Galvin, F. C.; Lloyd, S.; Mack, S. R.;
Owens, R.; Sabin, V.; Wynn, J. Bioorg. Med. Chem. Lett. 2007, 17, 562.
(c) Butler, J. R.; Wang, C.; Bian, J.; Ready, J. M. J. Am. Chem. Soc.
2011, 133, 9956. (d) Kiselev, E.; Sooryakumar, D.; Agama, K.;
Cushman, M.; Pommier, Y. J. Med. Chem. 2014, 57, 1289.
(3) (a) Lachkar, D.; Denizot, N.; Bernadat, G.; Ahamada, K.;
Beniddir, M. A.; Dumontet, V.; Gallard, J.-F.; Guillot, R.; Leblanc, K.;
N’nang, E. O.; Turpin, V.; Kouklovsky, C.; Poupon, E.; Evanno, L.;
Vincent, G. Nat. Chem. 2017, 9, 793. (b) Denizot, N.; Lachkar, D.;
Kouklovsky, C.; Poupon, E.; Evanno, L.; Vincent, G. Synthesis 2018,
50, 4229.
́
́
́
́
Vazquez-Romero, A.; Malmberg, J.; Johansson, M. J.; Gomez-Bengoa,
E.; Martín-Matute, B. ACS Catal. 2018, 8, 920. (d) Gong, W.; Zhou,
Z.; Shi, J.; Wu, B.; Huang, B.; Yi, W. Org. Lett. 2018, 20, 182−185.
(e) Sihag, P.; Jeganmohan, M. J. Org. Chem. 2019, 84, 2699.
(4) (a) De Sarkar, S. D.; Liu, W.; Kozhushkov, S. I.; Ackermann, L.
Adv. Synth. Catal. 2014, 356, 1461. (b) Cheng, G.; Li, T.-J.; Yu, J.-Q.
J. Am. Chem. Soc. 2015, 137, 10950. (c) Drapeau, M. P.; Gooßen, L. J.
Chem. - Eur. J. 2016, 22, 18654. (d) Li, H.; Jiang, Q.; Jie, X.; Shang,
Y.; Zhang, Y.; Goossen, L. J.; Su, W. ACS Catal. 2018, 8, 4777.
(e) Trita, A. S.; Biafora, A.; Drapeau, M. P.; Weber, P.; Gooßen, L. J.
Angew. Chem., Int. Ed. 2018, 57, 14580. (f) Dana, S.; Chowdhury, D.;
Mandal, A.; Chipem, F. A. S.; Baidya, M. ACS Catal. 2018, 8, 10173.
(g) Lv, W.; Wen, S.; Liu, J.; Cheng, G. J. Org. Chem. 2019, 84, 9786.
(h) Duarah, G.; Kaishap, P. P.; Begum, T.; Gogoi, S. Adv. Synth.
Catal. 2019, 361, 654.
(5) (a) Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565.
(b) Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010,
132, 6908. (c) Wang, H.; Grohmann, C.; Nimphius, C.; Glorius, F. J.
Am. Chem. Soc. 2012, 134, 19592. (d) Grigorjeva, L.; Daugulis, O.
Org. Lett. 2014, 16, 4684. (e) Webb, N. J.; Marsden, S. P.; Raw, S. A.
Org. Lett. 2014, 16, 4718. (f) Yu, D. G.; de Azambuja, F.; Glorius, F.
Angew. Chem., Int. Ed. 2014, 53, 2754. (g) Shi, L.; Yu, K.; Wang, B.
Chem. Commun. 2015, 51, 17277. (h) Upadhyay, N. S.; Thorat, V. H.;
E
Org. Lett. XXXX, XXX, XXX−XXX