Communication
ChemComm
measurements and structure refinements. X. W. and X. L. synthe-
sized several substrates. J. D. repeated some experiments. W. Y.
and Y. X. helped with modifying the manuscript and ESI.† Z. W.
conceived and directed the project, and drafted the manuscript
with assistance from all co-authors. All authors contributed to
discussions.
We acknowledge the Natural Science Foundation of Zhejiang
Province (Grant LY20B020012), the Fundamental Research Funds
for the Central Universities (2020CDJQY-A042), and the venture &
Innovation Support Program for Chongqing Overseas Returnees
10359–10363; (d) H. Zhang, B. Cheng and Z. Lu, Org. Lett., 2018, 20,
4028–4031; and some examples in ref. 5.
5
For selected examples, see: (a) Y. Huang, A. M. Walji, C. H. Larsen
and D. W. C. MacMillan, J. Am. Chem. Soc., 2005, 127, 15051–15053;
(b) H.-F. Cui, Y.-Q. Yang, Z. Chai, P. Li, C.-W. Zheng, S.-Z. Zhu and
G. Zhao, J. Org. Chem., 2010, 75, 117–122; (c) H. P. Shunatona,
N. Fr u¨ h, Y.-M. Wang, V. Rauniyar and F. D. Toste, Angew. Chem., Int.
Ed., 2013, 52, 7724–7727; (d) Z.-T. He, X. Jiang and J. F. Hartwig,
J. Am. Chem. Soc., 2019, 141, 13066–13073; (e) R. Ding, Z. A. De los
Santos and C. Wolf, ACS Catal., 2019, 9, 2169–2176; ( f ) H. Egami,
R. Hotta, M. Otsubo, T. Rouno, T. Niwa, K. Yamashita and
Y. Hamashima, Org. Lett., 2020, 22, 5656–5660; (g) B. M. Trost,
J. S. Tracy, T. Yusoontorn and C.-I. J. Hung, Angew. Chem., Int. Ed.,
2
020, 59, 2370–2374; (h) X.-J. Liu, S. Jin, W.-Y. Zhang, Q.-Q. Liu,
C. Zheng and S.-L. You, Angew. Chem., Int. Ed., 2020, 59,
039–2043.
(a) T. Tanaka, T. Kumamoto and T. Ishikawa, Tetrahedron Lett.,
000, 41, 10229; (b) E. Sekino, T. Kumamoto, T. Tanaka, T. Ikeda
(cx2019063).
2
6
Conflicts of interest
2
and T. Ishikawa, J. Org. Chem., 2004, 69, 2760; (c) U. Albrecht,
M. Lalk and P. Langer, Bioorg. Med. Chem., 2005, 13, 1531–1536;
There are no conflicts to declare.
(
d) I. N. Siddiqui, A. Zahoor, H. Hussain, I. Ahmed, V. U. Ahmad,
D. Padula, S. Draeger, B. Schulz, K. Meier, M. Steinert, T. Kurt ´a n,
U. Fl ¨o rke, G. Pescitelli and K. Krohn, J. Nat. Prod., 2011, 74, 365;
(e) S. Emami and Z. Ghanbarimasir, Eur. J. Med. Chem., 2015, 93,
539–563.
Notes and references
1
(a) K. Mueller, C. Faeh and F. Diederich, Science, 2007, 317,
881–1886; (b) S. Purser, P. R. Moore, S. Swallow and
1
V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320–330; (c) J. Wang,
M. S ´a nchez-Rosell ´o , J. L. Ace n˜ a, C. del Pozo, A. E. Sorochinsky,
S. Fustero, V. A. Soloshonok and H. Liu, Chem. Rev., 2014, 114,
7 (a) L.-G. Milroy, G. Zinzalla, G. Prencipe, P. Michel, S. V. Ley,
M. Gunaratnam, M. Beltran and S. Neidle, Angew. Chem., Int. Ed.,
2007, 46, 2493–2496; (b) C. Airoldi, F. Cardona, E. Sironi,
L. Colombo, M. Salmona, A. Silva, F. Nicotra and B. La Ferla, Chem.
Commun., 2011, 47, 10266–10268; (c) C.-A. Geng, Y.-B. Ma,
X.-M. Zhang, S.-Y. Yao, D.-Q. Xue, R.-P. Zhang and J.-J. Chen,
J. Agric. Food Chem., 2012, 60, 8197–8202; (d) S. Merlo, E. Sironi,
L. Colombo, F. Cardona, A. M. Martorana, M. Salmona, B. La Ferla
and C. Airoldi, ChemPlusChem, 2014, 79, 835–843; (e) C. Airoldi,
G. D’Orazio, B. Richichi, C. Guzzi, V. Baldoneschi, L. Colombo,
M. Salmona, C. Nativi, F. Nicotra and B. La Ferla, Chem. – Asian J.,
2016, 11, 299–309.
8 (a) M. Rueping and M.-Y. Lin, Chem. – Eur. J., 2010, 16, 4169–4172;
(b) Y.-H. Chen, X.-L. Sun, H.-S. Guan and Y.-K. Liu, J. Org. Chem.,
2017, 82, 4774–4783; (c) X.-J. Lv, W.-W. Zhao, Y.-H. Chen, S.-B. Wan
and Y.-K. Liu, Org. Chem. Front., 2019, 6, 1972–1976; (d) X. Lu,
Y. Zhang, Y. Wang, Y. Chen, W. Chen, R. Zhan, J. C. G. Zhao and
H. Huang, Adv. Synth. Catal., 2019, 361, 3234–3238.
9 (a) H.-F. Wang, H.-F. Cui, Z. Chai, P. Li, C.-W. Zheng, Y.-Q. Yang and
G. Zhao, Chem. – Eur. J., 2009, 15, 13299–13303; (b) Y. Zhao, Y. Pan,
H. Liu, Y. Yang, Z. Jiang and C.-H. Tan, Chem. – Eur. J., 2011, 17,
3571–3574; (c) X.-W. Du and L. M. Stanley, Org. Lett., 2015, 17,
3276–3279; (d) B. M. Trost, T. Saget, A. Lerchen and C.-I. Hung,
Angew. Chem., Int. Ed., 2016, 55, 781–784; (e) Y. Zhu, W. Zhang,
H. Mei, J. Han, V. A. Soloshonok and Y. Pan, Chem. – Eur. J., 2017,
23, 11221–11225; ( f ) V. Vaithiyanathan, M. J. Kim, Y. Liu, H. Yan
and C. E. Song, Chem. – Eur. J., 2017, 23, 1268–1272.
2
432–2506; (d) H. Mei, J. Han, S. Fustero, M. Medio-Simon,
D. M. Sedgwick, C. Santi, R. Ruzziconi and V. A. Soloshonok,
Chem. – Eur. J., 2019, 25, 11797–11819.
For selected reviews and examples for the construction of fluorine-
containing compounds, see: (a) J.-A. Ma and D. Cahard, Chem. Rev.,
2
2
004, 104, 6119–6146; (b) G. K. S. Prakash and P. Beier, Angew.
Chem., Int. Ed., 2006, 45, 2172–2174; (c) C. Bobbio and
V. Gouverneur, Org. Biomol. Chem., 2006, 4, 2065–2075;
(
2
d) S. Lectard, Y. Hamashima and M. Sodeoka, Adv. Synth. Catal.,
010, 352, 2708–2732; (e) Y. Zhao, Y. Pan, S.-B. D. Sim and C.-H. Tan,
Org. Biomol. Chem., 2012, 10, 479–485; ( f ) X. Yang, T. Wu,
R. J. Phipps and F. D. Toste, Chem. Rev., 2015, 115, 826–870;
(
g) S. Fustero, D. M. Sedgwick, R. Rom ´a n and P. Barrio, Chem.
Commun., 2018, 54, 9706–9725; (h) Y. Zhu, J. Han, J. Wang,
N. Shibata, M. Sodeoka, V. A. Soloshonok, J. A. S. Coelho and
F. D. Toste, Chem. Rev., 2018, 118, 3887–3964; (i) X.-Q. Chu, D. Ge,
M.-L. Wang, W. Rao, T.-P. Loh and Z.-L. Shen, Adv. Synth. Catal.,
2
2
019, 361, 4082–4090; ( j) A. Granados and A. Vallribera, Molecules,
020, 25, 3264; (k) X.-Q. Chu, T. Xie, Y.-W. Wang, X.-R. Li, W. Rao,
H. Xu and Z.-L. Shen, Chem. Commun., 2020, 56, 8699–8702;
l) S.-Z. Cai, D. Ge, L.-W. Sun, W. Rao, X. Wang, Z.-L. Shen and
(
X.-Q. Chu, Green Chem., 2021, 23, 935–941.
3
4
For selected examples using fluorinated nucleophiles, see:
(
a) G. Haufe, S. Bruns and M. Runge, J. Fluorine Chem., 2001, 112,
5
2
5–61; (b) M. H. Katcher, A. Sha and A. G. Doyle, J. Am. Chem. Soc., 10 (a) M. Lu, X. Wang, Z. Xiong, J. Duan, W. Ren, W. Yao, Y. Xia and
011, 133, 15902–15905; (c) J. Zhu, G. C. Tsui and M. Lautens, Angew.
Z. Wang, Adv. Synth. Catal., 2020, 362, 5524–5528; (b) Y.-T. Lai,
K. Nagaraju, R. Gurubrahamam and K. Chen, Adv. Synth. Catal.,
2020, 362, 3846–3850.
Chem., Int. Ed., 2012, 51, 12353–12356; (d) T. W. Butcher and
J. F. Hartwig, Angew. Chem., Int. Ed., 2018, 57, 13125–13129; and
some examples in ref. 5.
11 (a) K. L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht and
K. A. Jørgensen, Acc. Chem. Res., 2012, 45, 248–264; (b) L. Klier,
F. Tur, P. H. Poulsen and K. A. Jørgensen, Chem. Soc. Rev., 2017, 46,
1080–1102; (c) Z. Wang, Molecules, 2019, 24, 3418.
For selected examples using fluorinated electrophiles, see:
(
4
a) L. Hintermann and A. Togni, Angew. Chem., Int. Ed., 2000, 39,
359–4362; (b) R. Frantz, L. Hintermann, M. Perseghini, D. Broggini
and A. Togni, Org. Lett., 2003, 5, 1709–1712; (c) Y.-M. Zhao, 12 CCDC 2067319 (3al) contains the supplementary crystallographic
M. S. Cheung, Z. Lin and J. Sun, Angew. Chem., Int. Ed., 2012, 51, data for this paper.
This journal is © The Royal Society of Chemistry 2021
Chem. Commun., 2021, 57, 4722–4725 | 4725