10.1002/anie.202003897
Angewandte Chemie International Edition
RESEARCH ARTICLE
[1]
a) P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis, Reactivity,
Applications 2nd Edn, Wiley-VCH: Weinheim, 2014; b) J.-P. Bégué, D.
Bonnet-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, Wiley:
Hoboken, 2008; (c) J. Wang, M. Sꢀnchez-Rosellꢁ, J. L. Aceꢂa, C. d.
Pozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Liu, Chem.
Rev. 2014, 114, 2432.
2006, 47, 273; f) H. Ukigai, S. Hara, Tetrahedron Lett. 2016, 57, 1379;
g) Y. Xi, G. Zhu, L. Tang, S. Ma, D. Zhang, R. Zhang, G. He, H. Zhu,
Org. Biomol. Chem. 2017, 15, 7218; h) W.-X. Fan, J.-L. Li, W.-X. Lv, L.
Yang, Q. Li, H. Wang, Chem. Commun. 2020, 56, 82.
[15] a) J. Luo, Z. Zhu, Y. Liu, X. Zhao, Org. Lett. 2015, 17, 3620; b) X. Liu, R.
An, X. Zhang, J. Luo, X. Zhao, Angew. Chem. Int. Ed. 2016, 55, 5846;
c) X. Liu, Y. Liang, J. Ji, J. Luo, X. Zhao, J. Am. Chem. Soc. 2018, 140,
4782. d) Q. Cao, J. Luo, X. Zhao, Angew. Chem. Int. Ed. 2019, 58,
1315; e) Y. Liang, X. Zhao, ACS Catal. 2019, 9, 6896.
[2]
For selected examples, see: a) W. Chen, Z. Huang, N. E. S. Tay, B.
Giglio, M. Wang, H. Wang, Z. Wu, D. A. Nicewicz, Z. Li, Science, 2019,
364, 1170; b) T. Scattolin, S. Bouayad-Gervais, F. Schoenebeck,
Nature, 2019, 573, 102; c) X.-P. Fu, X.-S. Xue, X.-Y. Zhang, Y.-L. Xiao,
S. Zhang, Y.-L. Guo, X. Leng, K. N. Houk, X. Zhang, Nat. Chem. 2019,
11, 948; d) P. Adler, C. J. Teskey, D. Kaiser, M. Holy, H. H. Sitte, N.
Maulideꢃ, Nat. Chem. 2019, 11, 329.
[16] a) J. Luo, Q. Cao, X. Cao, X. Zhao, Nat. Commun. 2018, 9, 527; b) L.
Liao, H. Zhang, X. Zhao, ACS Catal. 2018, 8, 6745; c) Y. Liang, J. Ji, X.
Zhang, Q. Jiang, J. Luo, X. Zhao, Angew. Chem. Int. Ed. 2020, 59,
4959.
[3]
[4]
a) Y. Wang, J. Bolꢁs, N. Serradell, Drugs Future, 2006, 31, 788; b) Y. N.
Lamb, Drugs, 2017, 77, 1797.
[17] For selected chalcogenide-catalyzed examples reported by other
groups, see: a) S. E. Denmark, M. T. Burk, P. Natl Acad. Sci. USA,
2010, 107, 20655; b) S. E. Denmark, D. Kalyani, W. R. Collins, J. Am.
Chem. Soc. 2010, 132, 15752; c) X. Jiang, C. K. Tan, L. Zhou, Y.-Y.
Yeung, Angew. Chem. Int. Ed. 2012, 51, 7771; d) Y. Zhao, X. Jiang, Y.-
Y. Yeung, Angew. Chem. Int. Ed. 2013, 52, 8597; e) F. Chen, C. K. Tan,
Y.-Y. Yeung, J. Am. Chem. Soc. 2013, 135, 1232; f) R. C. Samanta, H.
Yamamoto, J. Am. Chem. Soc. 2017, 139, 1460; g) A. Roth, S. E.
Denmark, J. Am. Chem. Soc. 2019, 141, 13767; h) A. Matviitsuk, S. E.
Denmark, Angew.Chem. Int. Ed. 2019, 58, 12486; i) Y. Nishii, M. Ikeda,
Y. Hayashi, S. Kawauchi, M. Miura, J. Am. Chem. Soc. 2020, 142, 1621.
[18] For selected reviews, see: a) K. Uneyama, Organofluorine Chemistry,
Blackwell Publishing Ltd., Oxford, 2006, pp. 1–100; b) H. Amii, K.
Uneyama, Chem. Rev. 2009, 109, 2119; c) T. Stahl, H. F. T. Klare, M.
Oestreich, ACS Catal. 2013, 3, 1578; d) J.-D. Hamel, J.-F. Paquin,
Chem. Commun. 2018, 54, 10224.
a) M. Drouin, J.-D. Hamel, J.-F. Paquin, Synlett, 2016, 27, 821; b) X.
Pigeon, M. Bergeron, F. Barabé, P. Dubé, H. N. Frost, J.-F. Paquin,
Angew. Chem. Int. Ed. 2010, 49, 1123; c) M. Bergeron, T. Johnson, J.-
F. Paquin, Angew. Chem. Int. Ed. 2011, 50, 11112.
[5]
a) P. S. Fier, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 5524; b) Q.-Q.
Min, Z. Yin, Z. Feng, W.-H. Guo, X. Zhang, J. Am. Chem. Soc. 2014,
136, 1230; c) Y.-B. Yu, G.-Z. He, X. Zhang, Angew. Chem. Int. Ed.
2014, 53, 10457; d) Z. Feng, Q.-Q. Min, H.-Y. Zhao, J.-W. Gu, X. Zhang,
Angew. Chem. Int. Ed. 2015, 54, 1270; e) G. Li, T. Wang, F. Fei, Y.-M.
Su, Y. Li, Q. Lan, X.-S. Wang, Angew. Chem. Int. Ed. 2016, 55, 3491; f)
G. Wu, A. J. Wangelin, Chem. Sci. 2018, 9, 1795; g) W.-H. Guo, H.-Y.
Zhao, Z.-J. Luo, S. Zhang, X. Zhang, ACS Catal. 2019, 9, 38.
a) R. P. Singh, U. Majumder, J. M. Shreeve, J. Org. Chem. 2001, 66,
6263; b) Y. Matsumura, N. Mori, T. Nakano, H. Sasakura, T. Matsugi, H.
Hara, Y. Morizawa, Tetrahedron Lett. 2004, 45, 1527; c) J. M. Box, L. M.
Harwood, R. C. Whitehead, Synlett, 1997, 8, 571; d) T. Furuya, T.
Fukuhara, S. Hara, J. Fluorine Chem. 2005, 126, 721.
[6]
[7]
[19] a) D. Mandal, R. Gupta, R. D. Young, J. Am. Chem. Soc. 2018, 140,
10682; b) D. Mandal, R. Gupta, A. K. Jaiswal, R. D. Young, J. Am.
Chem. Soc. 2020, 142, 2572.
For other examples, see: a) B. Zhang, X. Zhang, Chem. Commun. 2016,
52, 1238; b) Z. Zhao, L. Racicot, G. K. Murphy, Angew. Chem. Int. Ed.
2017, 56, 11620; c) C.-Q. Wang, Y. Zhang, C. Feng, Angew. Chem. Int.
Ed. 2017, 56, 14918; d) X. Yang, Z.-H. Cao, Y. Zhou, F. Cheng, Z.-W.
Lin, Z. Ou, Ye. Yuan, Y.-Y. Huang, Org. Lett. 2018, 20, 2585; e) J.
Yang, J. Wang, H. Huang, G. Qin, Y. Jiang, T. Xiao, Org. Lett. 2019, 21,
2654.
[20] A. J. Cresswell, S. G. Davies, P. M. Roberts, J. E. Thomson, Chem.
Rev. 2015, 115, 566.
[21] a) K. Hirano, K. Fujita, H. Yorimitsu, H. Shinokubo, K. Oshima,
Tetrahedron Lett. 2004, 45, 2555; b) K. Hirano, H. Yorimitsu, K. Oshima,
Org. Lett. 2004, 6, 4873.
[22] a) F. Leroux, P. Jeschke, M. Schlosser, Chem. Rev. 2005, 105, 827; b)
K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881; c) G.
Landelle, A. Panossian, Curr. Top. Med. Chem. 2014, 14, 941.
[23] a) N. A. Meanwell, J. Med. Chem. 2011, 54, 2529; b) E. P. Gillis, K. J.
Eastman, M. D. Hill, D. J. Donnelly, N. A. Meanwell, J. Med. Chem.
2015, 58, 8315; c) N. A. Meanwell, J. Med. Chem. 2018, 61, 5822.
[24] For dimerization of dienes, see: a) R. Singh, S. K. Ghosh, Chem
Commun. 2011, 47, 10809; b) D. H. Dethe, R. D. Erande, B. D.
Dherange, Org. Lett. 2014, 16, 2764; c) S. Naskar, S. R. Chowdhury, S.
Mondal, D. K. Maiti, S. Mishra, I. Das, Org. Lett. 2019, 21, 1578.
[25] C. Xue, X. Jiang, C. Fu, S. Ma, Chem. Commun. 2013, 49, 5651.
[26] Both pathways can explain why only Z-type products are formed in the
reactions of secondary propargylic fluorides. For the discussion, see the
Supporting Information.
[8]
[9]
For selected reviews, see: a) D. A. Engel, G. B. Dudley, Org. Biomol.
Chem. 2009, 7, 4149; b) D. Roy, P. Tharra, B. Baire, Asian J. Org.
Chem. 2018, 7, 1015.
a) Y. Usuki, M. Iwaoka, S. Tomoda, Chem. Lett. 1992, 1507; b) G.
Zheng, J. Zhao, Z. Li, Q. Zhang, J. Sun, H. Sun, Q. Zhang, Chem. Eur.
J. 2016, 22, 3513; c) L. Pfeifer, V. Gouverneur, Org. Lett. 2018, 20,
1576; d) J. Xu, Y. Zhang, T. Qin, X. Zhao, Org. Lett. 2018, 20, 6384.
[10] a) J.-J. Wu, J. Xu, X. Zhao, Chem. Eur. J. 2016, 22, 15265; b) T.
Suꢀrez-Rodríguez, ꢄ. L. Suꢀrez-Sobrino, A. Ballesteros, J. Org. Chem.
2018, 83, 12575.
[11] For selected reviews, see: a) B. Sundararaju, M. Acharda, C. Bruneau,
Chem. Soc. Rev. 2012, 41, 4467; b) N. A. Butta, W. Zhang, Chem. Soc.
Rev. 2015, 44, 7929.
[27] D. O’Hagan, Chem. Soc. Rev. 2008, 37, 308.
[12] a) C. Hollingworth, A. Hazari, M. N. Hopkinson, M. Tredwell, E.
Benedetto, M. Huiban, A. D. Gee, J. M. Brown, V. Gouverneur, Angew.
Chem. Int. Ed. 2011, 50, 2613; b) M. H. Katcher, A. Sha, A. G. Doyle, J.
Am. Chem. Soc. 2011, 133, 15902; c) A. M. Lauer, J. Wu, Org. Lett.
2012, 14, 5138; d) Z. Zhang, F. Wang, X. Mu, P. Chen, G. Liu, Angew.
Chem. Int. Ed. 2013, 52, 7549; e) Q. Zhang, D. P. Stockdale, J. C.
Mixdorf, J. J. Topczewski, H. M. Nguyen, J. Am. Chem. Soc. 2015, 137,
11912.
[13] a) M. C. Pacheco, S. Purser, V. Gouverneur, Chem. Rev. 2008, 108,
1943; for selected examples about reactions of propargylic fluorides,
see: b) F. Benayoud, L. Chen, G. A. Moniz, A. J. Zapata, G. B.
Hammond. Tetrahedron, 1998, 54, 15541; c) V. Madiot, D. Grée, R.
Grée, Tetrahedron Lett. 1999, 40, 6403; d) J.-D. Hamel, M. Beaudoin,
M. Cloutier, J.-F. Paquin, Synlett, 2017, 28, 2823.
[14] a) S. Rozen, M. Brand, J. Org. Chem. 1986, 51, 222; b) J. Barluenga,
M. A. Rodríguez, J. M. Gonzꢀlez, P. J. Campos, G. Asensio,
Tetrahedron Lett. 1986, 27, 3303; c) D. F. Shellhamer, B. C. Jones, B. J.
Pettus, T. L. Pettus, J. M. Stringer, V. L. Heasley, J. Fluorine Chem.
1998, 88, 37; d) P. Conte, B. Panunzi, M. Tingoli, Tetrahedron Lett.
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