Communication
ChemComm
Int. Ed., 2017, 56, 14918; (d) F. Romanov-Michailidis, B. D. Ravetz,
D. W. Paley and T. Rovis, J. Am. Chem. Soc., 2018, 140, 5370.
12 J.-D. Hamel, T. Hayashi, M. Cloutier, P. R. Savoie, O. Thibeault,
M. Beaudoin and J.-F. Paquin, Org. Biomol. Chem., 2017, 15, 9830.
13 For the related intramolecular cyclization, see: J.-D. Hamel and
J.-F. Paquin, J. Fluorine Chem., 2018, 216, 11.
14 For Au-catalyzed reactions of substrates bearing other fluorinated
substituents than a difluoromethylene unit at the propargylic position,
see: (a) M. Cloutier, M. Roudias and J.-F. Paquin, Org. Lett., 2019,
21, 3866; (b) R. Gauthier, M. Mamone and J.-F. Paquin, Org. Lett., 2019,
21, 9024.
Notes and references
1 For selected reviews on gold chemistry and its applications: (a) A. S. K.
Hashmi, Chem. Rev., 2007, 107, 3180; (b) W. Yang and A. S. K. Hashmi,
Chem. Soc. Rev., 2014, 43, 2941; (c) R. Dorel and A. M. Echavarren,
¨
Chem. Rev., 2015, 115, 9028; (d) D. Pflasterer and A. S. K. Hashmi,
Chem. Soc. Rev., 2016, 45, 1331.
2 Review: J. A. Goddwin and A. Aponick, Chem. Commun., 2015,
51, 8730.
3 For selected examples of biased substrates in Au-catalyzed hydration
and hydroalkoxylation of disubstituted alkynes, see: (a) W. Wang,
B. Xu and G. B. Hammond, J. Org. Chem., 2009, 74, 1640; (b) M. R.
Kuram, M. Bhanuchandra and A. K. Sahoo, J. Org. Chem., 2010, 75,
2247; (c) J. Jeong, D. Ray and C. Oh, Synlett, 2012, 897; (d) Y. Oonishi,
15 For a review on the successful combination of fluorine chemistry
´
and gold catalysis, see: J. Miro and C. del Pozo, Chem. Rev., 2016,
116, 11924.
´
´
A. Gomez-Suarez, A. R. Martin and S. P. Nolan, Angew. Chem., Int.
Ed., 2013, 52, 9767.
16 For recent reviews on synthetic approaches to difluoromethylene-
containing compounds, see: (a) X. Yang, T. Wu, R. J. Phipps and
F. D. Toste, Chem. Rev., 2015, 115, 826; (b) M.-C. Belhomme, T. Besset,
T. Poisson and X. Pannecoucke, Chem. – Eur. J., 2015, 21, 12836; (c) X. Pan,
H. Xia and J. Wu, Org. Chem. Front., 2016, 3, 1163; (d) J. Rong, C. Ni and
J. Hu, Asian J. Org. Chem., 2017, 6, 139; (e) W. Zhang and Y. Wang,
Tetrahedron Lett., 2018, 59, 1301; ( f ) E. Carbonnel, T. Poisson, P. Jubault,
X. Pannecoucke and T. Besset, Front. Chem., 2019, 7, 111.
17 For selected example, see: (a) M. Skibinski, Y. Wang, A. M. Z. Slawin,
T. Lebl, P. Kirsch and D. O’Hagan, Angew. Chem., Int. Ed., 2011,
50, 10581; (b) C. A. Urbina-Blanco, M. Skibinski, D. O’Hagan and
S. P. Nolan, Chem. Commun., 2013, 49, 7201; (c) R. Callejo, M. J. Corr,
M. Yang, M. Wang, D. B. Cordes, A. M. Z. Slawin and D. O’Hagan,
Chem. – Eur. J., 2016, 22, 8137.
4 L. Xie, Y. Wu, W. Yi, L. Zhu, J. Xiang and W. He, J. Org. Chem., 2013,
78, 9190.
5 The same reaction using a heterogeneous gold catalyst has been
reported, see: S. Hu, D. Liu, C. Yan and M. Cai, Synth. Commun.,
2018, 48, 2983.
6 This regioselectivity is also observed in the gold-catalyzed C-addition
of phenol to haloalkynes, see: T. Adak, J. Schulmeister, M. C. Dietl,
M. Rudolph, F. Rominger and A. S. K. Hashmi, Eur. J. Org. Chem., 2019,
3867.
7 D. O’Hagan, Chem. Soc. Rev., 2008, 37, 308.
8 Selected recent reviews: (a) E. P. Gillis, K. J. Eastman, M. D. Hill,
D. J. Donnelly and N. A. Meanwell, J. Med. Chem., 2015, 58, 8315;
˜
(b) Y. Zhou, J. Wang, Z. Gu, S. Wang, W. Zhu, J. L. Acena,
18 For example, see: (a) T. Taguchi, T. Morikawa, O. Kitagawa,
T. Mishima and Y. Kobayashi, Chem. Pharm. Bull., 1985, 33, 5137;
V. A. Soloshonok, K. Izawa and H. Liu, Chem. Rev., 2016, 116, 422;
(c) N. A. Meanwell, J. Med. Chem., 2018, 61, 5822; (d) Fluorine in Life
Sciences: Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals,
ed. G. Haufe and F. R. Leroux, Elsevier, London, UK, 2019.
´
(b) O. Paleta, V. Dadak, V. Dedek and H.-J. Timpe, J. Fluorine Chem.,
´
1988, 39, 397; (c) M. P. Bosch, R. Perez, G. Lahuerta, D. Hernanz,
F. Camps and A. Guerrero, Bioorg. Med. Chem., 1996, 4, 467;
(d) O. Cohen and S. Rozen, Tetrahedron, 2008, 64, 5362;
(e) V. Hugenberg and G. Haufe, J. Fluorine Chem., 2010, 131, 942.
19 Similar experiments were performed with chloroalkyne 1a and
similar trends where observed.
9 Selected reviews: (a) T. Fujiwara and D. O’Hagan, J. Fluorine Chem.,
2014, 167, 16; (b) P. Jeschke, Pest Manage. Sci., 2017, 73, 1053.
10 For reviews on the influence of fluorine substitution on reactivity,
see: (a) D. Cahard and V. Bizet, Chem. Soc. Rev., 2014, 43, 135;
(b) C. Ni and J. Hu, Chem. Soc. Rev., 2016, 45, 5441; (c) D. L. Orsia
and R. A. Altman, Chem. Commun., 2017, 53, 7168.
´
20 (a) A. Guerinot, W. Fang, M. Sircoglou, C. Bour, S. Bezzenine-
´
Lafollee and V. Gandon, Angew. Chem., Int. Ed., 2013, 52, 5848;
11 For recent examples, see: (a) J. Takaya, S. Ito, H. Nomoto, N. Saito,
N. Kirai and N. Iwasawa, Chem. Commun., 2015, 51, 17662; (b) J. V.
Obligacion, M. J. Bezdek and P. J. Chirik, J. Am. Chem. Soc., 2017,
139, 2825; (c) C.-Q. Wang, Y. Zhang and C. Feng, Angew. Chem.,
´
´
(b) W. Fang, M. Presset, A. Guerinot, C. Bour, S. Bezzenine-Lafollee
and V. Gandon, Chem. – Eur. J., 2014, 20, 5439.
21 D. C. Rosenfeld, S. Shekhar, A. Takemiya, M. Utsunomiya and
J. F. Hartwig, Org. Lett., 2006, 8, 4179.
Chem. Commun.
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