10.1002/anie.202006720
Angewandte Chemie International Edition
RESEARCH ARTICLE
16076; c) A. Cartier, E. Levernier, A. L. Dhimane, T. Fukuyama, C. Ollivier,
I. Ryu, L. Fensterbank, Adv. Synth. Catal. 2020, 362, 2254.
mixture.; c) We also posit that the excess alkyliodide may be implicated in
the radical propagation step as shown in Scheme 2(c), Path C, promoting
conversion of the a-hydroxy radical intermediate (83) to the amide product. .
[25] C. P. Andrieux, I. Gallardo, J.-M. Savéant, K.-B. Su, J. Am. Chem. Soc.
1986, 108, 638.
[13] For selected examples and reviews on multi-photon excitation see: a) I.
Ghosh, T. Ghosh, J. I. Bardagi, B. König, Science 2014, 346, 725; b) B. D.
Ravetz, A. B. Pun, E. M. Churchill, D. N. Congreve, T. Rovis, L. M. Campos,
Nature 2019, 565, 343; c) M. Giedyk, R. Narobe, S. Weiß, D. Touraud, W.
Kunz, B. König, Nat. Catal. 2020, 3, 40; d) A. Chatterjee, B. König, Angew.
Chem. Int. Ed. 2019, 131, 14427; e) I. Ghosh, B. König, Angew. Chem. Int.
Ed. 2016, 55, 7676; f) F. Glaser, C. Kerzig, O. S. Wenger, Angew. Chem.
Int. Ed. 2020, 59, 2; g) C. Kerzig, G. Xingwei, O. S. Wenger, J. Am. Chem.
Soc. 2019, 141, 2122.
[26] a) D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965; b) M.
Corbet, F. De Campo, Angew. Chem. Int. Ed. 2013, 52, 9896; c) C.
Sambiagio, D. Schönbauer, R. Blieck, T. Dao-Huy, G. Pototschnig, P.
Schaaf, T. Wiesinger, M. F. Zia, J. Wencel-Delord, T. Besset, B. U. W.
Maes, M. Schnürch, Chem. Soc. Rev. 2018, 47, 6603.
[27] a) J. J. Devery III, J. D. Nguyen, C. Dai, C. R. J. Stephenson, ACS Catal.
2016, 6, 5962; b) Y. Shen, J. Cornella, F. Juliá-Hernández, R. Martin, ACS
Catal. 2017, 7, 409; c) N. B. Bissonnette, M. J. Boyd, G. D. May, S. Giroux,
P. Nuhant, J. Org. Chem. 2018, 83, 10933; d) D. Alpers, K. P. Cole, C. R.
J. Stephenson, Angew. Chem. Int. Ed. 2018, 57, 12167.
[14] T. U. Connell, C. L. Fraser, M. L. Czyz, Z. M. Smith, D. J. Hayne, E. H.
Doeven, J. Agugiaro, D. J. D. Wilson, J. L. Adcock, A. D. Scully, D. E.
Gómez, N. W. Barnett, A. Polyzos, P. S. Francis, J. Am. Chem. Soc. 2019,
141, 17646.
[15] I. A. MacKenzie, L. Wang, N. P. R. Onuska, O. F. Williams, K. Begam, A.
M. Moran, B. D. Dunietz, D. A. Nicewicz, Nature 2020, 580, 76.
[28] a) C. Gosset, S. Pellegrini, R. Jooris, T. Bousquet, L. Pelinski, Adv. Synth.
Catal. 2018, 360, 3401; b) J.-B. Peng, X. Qi, X.-F. Wu, ChemSusChem
2016, 9, 2279.
[16] For selected reviews and examples on flow chemistry see: a) S. V. Ley, D.
E. Fitzpatrick, R. J. Ingham, R. M. Myers, Angew. Chem. Int. Ed. 2015, 54,
3449; b) J. C. Pastre, D. L. Browne, S. V. Ley, Chem. Soc. Rev. 2013, 42,
8849; c) V. Hessel, D. Kralisch, N. Kockmann, T. Noël, Q. Wang,
ChemSusChem 2013, 6, 746; d) B. Gutmann, D. Cantillo, C. O. Kappe,
Angew. Chem. Int. Ed. 2015, 54, 6688; e) D. Webb, T. F. Jamison, Chem.
Sci. 2010, 1, 675; f) M. B. Plutschack, B. Pieber, K. Gilmore, P. H.
Seeberger, Chem. Rev. 2017, 117, 11796; g) I. R. Baxendale, J. Chem.
Technol. Biotechnol. 2013, 88, 519; h) T. Tsubogo, H. Oyamada, S.
Kobayashi, Nature 2015, 520, 329; i) J. L. Howard, C. Schotten, D. L.
Browne, React. Chem. Eng. 2017, 2, 281.
[29] a) H. Matsubara, I. Ryu, C. H. Schiesser, Org. Biomol. Chem. 2007, 5,
3320; b) K. Nagahara, I. Ryu, M. Komatsu, N. Sonoda, J. Am. Chem. Soc.
1997, 119, 5465.
[30] T. Kawamoto, A. Sato, I. Ryu, Chem. Eur. J. 2015, 21, 14764.
[31] T. Kawamoto, H. Matsubara, T. Fukuyama, I. Ryu, Chem. Lett. 2018, 47,
1169.
[17] For selected reviews and applications of the tube-in-tube reactor see: a) M.
O’Brien, I. R. Baxendale, S. V. Ley, Org. Lett. 2010, 12, 1596; b) A. Polyzos,
M. O'Brien, T. P. Petersen, I. R. Baxendale, S. V. Ley, Angew. Chem. Int.
Ed. 2011, 50, 1190; c) M. Brzozowski, M. O'Brien, S. V. Ley, A. Polyzos,
Acc. Chem. Res. 2015, 48, 349; d) C. J. Mallia, I. R. Baxendale, Org.
Process Res. Dev. 2016, 20, 327.
[18] For selected applications of the tube-in-tube reactor in carbonylation
reactions see: a) N. Micic, A. Polyzos, Org. Lett. 2018, 20, 4663; b) U.
Gross, P. Koos, M. O'Brien, A. Polyzos, S. V. Ley, Eur. J. Org. Chem. 2014,
6418; c) P. Koos, U. Gross, A. Polyzos, M. O'Brien, I. Baxendale, S. V. Ley,
Org. Biomol. Chem. 2011, 9, 6903; d) C. J. Mallia, G. C. Walter, I. R.
Baxendale, Beilstein J. Org. Chem. 2016, 12, 1503; e) C. Brancour, T.
Fukuyama, Y. Mukai, T. Skrydstrup, I. Ryu, Org. Lett. 2013, 15, 2794.
[19] L. Ren, L. Xinwei, N. Jiao, Org. Lett. 2016, 18, 5852.
[20] a) J. R. Martinelli, T. P. Clark, D. A. Watson, R. H. Munday, S. L. Buchwald,
Angew. Chem. Int. Ed. 2007, 46, 8460; b) R. J. Perry, D. B. Wilson, J. Org.
Chem. 1996, 61, 7482; c) P.-L. Lagueux-Tremblay, A. Fabrikant, B. A.
Arndsten, ACS Catal. 2018, 8, 5350.
[21]a) T. Morack, C. Mück-Lichtenfeld, R. Gilmour, Angew. Chem. Int. Ed. 2019,
58, 1208; b) M. Zhang, R. Ruzi, J. Xi, N. Li, Z. Wu, W. Li, S. Yu, C. Zhu,
Org. Lett. 2017, 19, 3430; c) G. Goti, B. Bieszczad, A. Vega-Peñaloza, P.
Melchiorre, Angew. Chem. Int. Ed. 2019, 58, 1213.
[22] a) J. I. M. Alvarado, A. B. Ertel, A. Stegner, E. E. Stache, A. G. Doyle, Org.
Lett. 2019, 21, 9940; b) X. Fan, T. Lei, B. Chen, C.-H. Tung, L.-Z. Wu, Org.
Lett. 2019, 21, 4153; c) I. Ryu, A. Tani, T. Fukuyama, D. Ravelli, M. Fagnoni,
A. Albini, Angew. Chem. Int. Ed. 2011, 50, 1869; d) A. Cartier, E. Levernier,
V. Corcé, T. Fukuyama, A. L. Dhimane, C. Ollivier, I. Ryu, L. Fensterbank,
Angew. Chem. Int. Ed. 2019, 131, 1803.
[23] Y. Uozumi, T. Arii, T. Watanabe, J. Org. Chem. 2001, 66, 5272.
[24] The excess equivalent of alkyl iodide may be accounted as follows: a)
Remains unreacted. For example, for the synthesis of amide 32, 67% of
the excess was recovered following chromatographic isolation; b)
protodehalogenation according 1H NMR analysis of the crude reaction
9
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