F
F.-F. Pan et al.
Special Topic
Synthesis
1,2-Bis(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)eth-
ane (2r)
Acknowledgment
We acknowledge the NMR facility at SKLAOC, and Mr. Fengming Qi for
his expert assistance.
Yield: 61.8 mg (68%); white solid; mp: 111–113 °C.
1H NMR (400 MHz, CDCl3): = 7.05 (d, J = 8.1 Hz, 2 H), 6.71 (dd, J = 8.1,
1.8 Hz, 2 H), 6.63 (d, J = 1.8 Hz, 2 H), 6.58 (t, J = 75.8 Hz, 2 H), 3.78 (t,
J = 6.9 Hz, 4 H), 2.84 (s, 4 H), 1.28–1.17 (m, 2 H), 0.66–0.59 (m, 4 H),
0.35–0.30 (m, 4 H).
Supporting Information
13C NMR (100 MHz, CDCl3): = 150.4, 140.2, 138.8, 122.8, 121.1, 116.5
(t, J = 257.5 Hz), 115.1, 74.0, 37.7, 10.3, 3.2.
Supporting information for this article is available online at
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19F NMR (376 MHz, CDCl3): = –81.6.
IR (neat): 3016, 2930, 2868, 1600, 1514, 1391, 1261, 1217, 1135,
References
1025, 1008, 829, 635 cm–1
.
(1) (a) Barrett, T. N.; Braddock, D. C.; Monta, A.; Webb, M. R.; White,
A. J. P. J. Nat. Prod. 2011, 74, 1980. (b) Zhu, L.-J.; Wang, M.-Q.;
Qin, Y.; Wang, M.-N.; Zhang, G.-Q.; Niu, L.-T.; Chen, J.-B.; Zhang,
X.; Yao, X.-S. J. Asian Nat. Prod. Res. 2020, in press DOI:
10.1080/10286020.2020.1826937.
(2) (a) Iwasa, E.; Hamashima, Y.; Fujishiro, S.; Hashizume, D.;
Sodeoka, M. Tetrahedron 2011, 67, 6587. (b) Duan, X.-J.; Li, X.-
M.; Wang, B.-G. J. Nat. Prod. 2007, 70, 1210.
HRMS (ESI): m/z [M + Na]+ calcd. for C24H26F4NaO4: 477.1659; found:
477.1674.
1,1,2,2-Tetraphenylethane (2s, known)27
Yield: 56.2 mg (84%); white solid; mp: 228–231 °C.
1H NMR (400 MHz, CDCl3): = 7.16 (d, J = 7.4 Hz, 8 H), 7.09 (t, J = 7.6
Hz, 8 H), 6.99 (t, J = 7.2 Hz, 4 H), 4.77 (s, 2 H).
(3) (a) Goldup, S. M.; Leigh, D. A.; McBurney, R. T.; McGonigal, P. R.;
Plant, A. Chem. Sci. 2010, 1, 383. (b) Prinsell, M. R.; Everson, D.
A.; Weix, D. J. Chem. Commun. 2010, 46, 5743. (c) Mboyi, C. D.;
Gaillard, S.; Mabaye, M. D.; Pannetier, N.; Renaud, J.-L. Tetrahe-
dron 2013, 69, 4875. (d) Khan, S.; Ghatak, A.; Bhar, S. Tetrahe-
dron Lett. 2015, 56, 2480. (e) Liu, Y.; Xiao, S.; Qi, Y.; Du, F. Chem.
Asian J. 2017, 12, 673.
(4) Cai, Y.; Qian, X.; Gosmini, C. Adv. Synth. Catal. 2016, 358, 2427.
(5) Barrero, A. F.; Herrador, M. M.; Quílez del Moral, J. F.; Arteaga,
P.; Akssira, M.; El Hanbali, F.; Arteaga, J. F.; Diéguez, H. R.;
Sánchez, E. M. J. Org. Chem. 2007, 72, 2251.
13C NMR (100 MHz, CDCl3): = 143.6, 128.6, 128.3, 126.0, 56.4.
IR (neat): 3027, 1493, 1450, 1072, 1031, 746, 695 cm–1
.
1,1,2,2-Tetra-p-tolylethane (2t, known)27
Yield: 59.4 mg (76%); white solid; mp: 286–289 °C.
1H NMR (400 MHz, CDCl3): = 7.04 (d, J = 8.0 Hz, 8 H), 6.89 (d, J = 8.0
Hz, 8 H), 4.68 (s, 2 H), 2.16 (s, 12 H).
13C NMR (100 MHz, CDCl3): = 141.2, 135.0, 129.0, 128.3, 55.5, 21.1.
IR (neat): 2920, 1513, 1182, 1120, 801, 751 cm–1
.
(6) Liu, Y.; Zhang, D.; Xiao, S.; Qi, Y.; Liu, S. Asian J. Org. Chem. 2019,
8, 858.
1,2-Diphenyl-1,2-di-p-tolylethane (2u, known)28
(7) Xu, X.; Cheng, D.; Pei, W. J. Org. Chem. 2006, 71, 6637.
(8) Sato, K.; Inoue, Y.; Mori, T.; Sakaue, A.; Tarui, A.; Omote, M.;
Kumadaki, I.; Ando, A. Org. Lett. 2014, 16, 3756.
Yield: 66.7 mg (92%); white solid; mp: 203–206 °C.
1H NMR (400 MHz, CDCl3): = 7.18–7.02 (m, 24 H), 7.00–6.86 (m, 12
H), 4.72 (s, 4 H), 2.15 (s, 6 H), 2.14 (s, 6 H).
13C NMR (100 MHz, CDCl3): = 144.05, 143.99, 140.67, 140.61, 135.2,
129.02, 128.97, 128.5, 128.4, 128.23, 128.19, 125.8, 56.0, 21.10, 21.07.
IR (neat): 3027, 2920, 1515, 1495, 1452, 727, 695 cm–1
(9) (a) Lei, A.; Zhang, X. Org. Lett. 2002, 4, 2285. (b) Cahiez, G.;
Moyeux, A.; Buendia, J.; Duplais, C. J. Am. Chem. Soc. 2007, 129,
13788. (c) Zhou, Z.; Xue, W. J. Organomet. Chem. 2009, 694, 599.
(d) Zhu, Y.; Xiong, T.; Han, W.; Shi, Y. Org. Lett. 2014, 16, 6144.
(10) Cao, Z.-C.; Shi, Z.-J. J. Am. Chem. Soc. 2017, 139, 6546.
(11) (a) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling
Reactions; Wiley-VCH: Weinheim, 1998. (b) Kuwano, R. Synthe-
sis 2009, 7, 1049. (c) Su, B.; Cao, Z.-C.; Shi, Z.-J. Acc. Chem. Res.
2015, 48, 886. (d) Tobisu, M.; Chatani, N. Acc. Chem. Res. 2015,
48, 1717. (e) Tollefson, E. J.; Hanna, L. E.; Jarvo, E. R. Acc. Chem.
Res. 2015, 48, 2344.
(12) (a) A review: Pang, X.; Peng, X.; Shu, X.-Z. Synthesis 2020, 52,
3751. Selected examples: (b) Qian, X.; Auffrant, A.; Felouat, A.;
Gosmini, C. Angew. Chem. Int. Ed. 2011, 50, 10402. (c) Ackerman,
L. K. G.; Anka-Lufford, L. L.; Naodovic, M.; Weix, D. J. Chem. Sci.
2015, 6, 1115. (d) Tollefson, E. J.; Erickson, L. W.; Jarvo, E. R.
J. Am. Chem. Soc. 2015, 137, 9760. (e) Yan, X.-B.; Li, C.-L.; Jin, W.-
J.; Guo, P.; Shu, X.-Z. Chem. Sci. 2018, 9, 4529. (f) Ye, Y.; Chen, H.;
Sessler, J. L.; Gong, H. J. Am. Chem. Soc. 2019, 141, 820.
(13) Metal-catalyzed hydrogen-borrowing reactions: (a) Yang, Q.;
Wang, Q.; Yu, Z. Chem. Soc. Rev. 2015, 44, 2305. (b) Corma, A.;
Navas, J.; Sabater, M. J. Chem. Rev. 2018, 118, 1410.
.
1,1,2,2-Tetrakis(4-fluorophenyl)ethane (2v, known)27
Yield: 69.5 mg (86%); white solid; mp: 311–314 °C.
1H NMR (400 MHz, CDCl3): = 7.07–7.01 (m, 8 H), 6.86–6.79 (m, 8 H),
4.62 (s, 2 H).
13C NMR (100 MHz, CDCl3): = 161.3 (d, JC–F = 246.1 Hz), 138.7 (d, JC–F
3.2 Hz), 129.9 (d, JC–F = 7.9 Hz), 115.4 (d, JC–F = 21.4 Hz), 55.3.
19F NMR (376 MHz, CDCl3): = –116.5.
=
IR (neat): 2920, 1605, 1510, 1234, 1159, 1096, 1016, 826, 770 cm–1
.
Conflict of Interest
The authors declare no conflict of interest.
Funding Information
(14) Ru-catalyzed dehydroxylative reactions: (a) Lee, D.-H.; Kwon, K.-
H.; Yi, C. S. Science 2011, 333, 1613. (b) Lee, D.-H.; Kwon, K.-H.; Yi,
C. S. J. Am. Chem. Soc. 2012, 134, 7325.
We thank the National Natural Science Foundation of China for their
financial support (21772072, 22071084).Natio
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