G
Synthesis
J. Malineni et al.
Special Topic
Methyl 4-(Naphthalen-2-yl)benzoate
(4) (a) Percec, V.; Bae, J. Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060.
(
6
b) Percec, V.; Bae, J. Y.; Zhao, M. Y.; Hill, D. H. J. Org. Chem. 1995,
0, 1066. (c) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O.
The product was obtained as a white solid (from OMs: 77 mg, 98%;
from OSO NMe : 78 mg, 99%; from OPiv: 76 mg, 97%; from OBoc: 77
2
2
J. Org. Chem. 2004, 69, 3447. (d) Zim, D.; Lando, V. R.; Dupont, J.;
Monteiro, A. L. Org. Lett. 2001, 3, 3049. (e) Gao, H.; Li, Y.; Zhou,
Y. G.; Han, F. S.; Lin, Y. J. Adv. Synth. Catal. 2011, 353, 309.
mg, 98%; from OCONEt : 77 mg, 98%; from OMe: 77 mg, 98%) after
column chromatography on silica gel [hexane–EtOAc, 95:5 (v/v)]; mp
2
1
49–150 °C; R = 0.42 [silica gel, hexane–EtOAc, 9:1 (v/v)].
f
(
f) Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531.
5) (a) Baghbanzadeh, M.; Pilger, C.; Kappe, C. O. J. Org. Chem. 2011,
6, 1507. (b) Quasdorf, K. W.; Antoft-Finch, A.; Liu, P.;
1
H NMR (500 MHz, CDCl ): δ = 8.16 (d, J = 8.3 Hz, 2 H), 8.09 (s, 1 H),
3
(
7.96–7.86 (m, 3 H), 7.79 (d, J = 8.3 Hz, 2 H), 7.76 (dd, J = 8.5, 1.6 Hz, 1
7
H), 7.56–7.50 (m, 2 H), 3.97 (s, 3 H).
Silberstein, A. L.; Komaromi, A.; Blackburn, T.; Ramgren, S. D.;
Houk, K. N.; Snieckus, V.; Garg, N. K. J. Am. Chem. Soc. 2011, 133,
13
C NMR (126 MHz, CDCl ): δ = 167.02, 145.55, 137.30, 133.59,
3
133.02, 130.20, 128.97, 128.69, 128.37, 127.71, 127.30, 126.55,
6
352. (c) Chen, G.-J.; Han, F.-S. Eur. J. Org. Chem. 2012, 3575.
d) Ke, H.; Chen, X.; Zou, G. J. Org. Chem. 2014, 79, 7132.
(6) (a) Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008,
30, 14422. (b) Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J.
126.44, 126.36, 125.24, 52.15.
(
+
MS (GS–MS): m/z [M] calcd for C18H14O : 262.1; found: 262.5.
2
1
J. Am. Chem. Soc. 2008, 130, 14468.
2
-(4-Methoxyphenyl)naphthalene
(
(
7) Kuwano, R.; Shimizu, R. Chem. Lett. 2011, 40, 913.
8) James, C. A.; Coelho, A. L.; Gevaert, M.; Forgione, P.; Snieckus, V.
J. Org. Chem. 2009, 74, 4094.
The product was obtained as a white solid (from OMs: 69 mg, 98%;
from OSO NMe : 69 mg, 98%; from OPiv: 67 mg, 96%; from OBoc: 69
mg, 98%; from OCONEt : 69 mg, 98%; from OMe: 67 mg, 95%) after
2
2
2
(
9) (a) Zhao, Y. L.; Li, Y.; Li, Y.; Gao, L. X.; Han, F. S. Chem. Eur. J.
column chromatography on silica gel [hexane–EtOAc, 95:5 (v/v)]; mp
2010, 16, 4991. (b) Chen, H.; Huang, Z. B.; Hu, X. M.; Tang, G.;
130−131 °C; R = 0.58 [silica gel, hexane–EtOAc, 9:1 (v/v)].
f
Xu, P. X.; Zhao, Y. F.; Cheng, C. H. J. Org. Chem. 2011, 76, 2338.
(c) Liu, L.; Zhang, S.; Chen, H.; Lv, Y.; Zhu, J.; Zhao, Y. Chem.
Asian J. 2013, 8, 2592.
1
H NMR (500 MHz, CDCl ): δ = 8.02 (s, 1 H), 7.92–7.87 (m, 3 H), 7.75
3
(d, J = 8.3 Hz, 1 H), 7.69 (d, J = 8.3 Hz, 2 H), 7.53–7.47 (m, 2 H), 7.05 (d,
J = 8.4 Hz, 2 H), 3.89 (s, 3 H).
(
10) (a) Tang, Z. Y.; Hu, Q. S. J. Am. Chem. Soc. 2004, 126, 3058.
(b) Wilson, D. A.; Wilson, C. J.; Rosen, B. M.; Percec, V. Org. Lett.
2008, 10, 4879. (c) LaBerge, N. A.; Love, J. A. Eur. J. Org. Chem.
2015, 5546. (d) Niwa, T.; Ochiai, H.; Watanabe, Y.; Hosoya, T.
J. Am. Chem. Soc. 2015, 137, 14313. (e) Hansen, A. L.; Ebran, J.-P.;
Gøgsig, T. M.; Skrydstrup, T. Chem. Commun. 2006, 4137.
13
C NMR (126 MHz, CDCl ): δ = 159.31, 138.20, 133.82, 133.67,
3
132.37, 128.46, 128.39, 128.10, 127.67, 126.27, 125.68, 125.47,
125.07, 114.37, 55.40.
+
MS (GS–MS): m/z [M] calcd for C17H14O: 234.1; found: 234.2.
(f) Dürr, A. B.; Yin, G.; Kalvet, I.; Napoly, F.; Schoenebeck, F.
Chem. Sci. 2016, 1076. (g) Yu, D.; Wang, C.; Yao, C.; Shen, Q.; Lu,
L. Org. Lett. 2014, 16, 5544.
Acknowledgment
(
(
11) Molander, G. A.; Beaumard, F. Org. Lett. 2010, 12, 4022.
12) (a) Leowanawat, P.; Zhang, N.; Resmerita, A.-M.; Rosen, B. M.;
Percec, V. J. Org. Chem. 2011, 76, 9946. (b) Leowanawat, P.;
Zhang, N.; Percec, V. J. Org. Chem. 2012, 77, 1018.
Financial support by the National Science Foundation (DMR-1066116,
DMR-1120901 and OISE-1243313), the P. Roy Vagelos Chair at the
University of Pennsylvania and the Humboldt Foundation is gratefully
acknowledged.
(13) (a) Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem. Int. Ed.
2008, 47, 4866. (b) Zarate, C.; Manzano, R.; Martin, R. J. Am.
Chem. Soc. 2015, 137, 6754.
Supporting Information
(
14) Leowanawat, P.; Zhang, N.; Safi, M.; Hoffman, D. J.; Fryberger,
M. C.; George, A.; Percec, V. J. Org. Chem. 2012, 77, 2885.
15) (a) Xing, C.-H.; Lee, J.-R.; Tang, Z.-Y.; Zheng, J. R.; Hu, Q.-S. Adv.
Synth. Catal. 2011, 353, 2051. (b) Hu, F.; Lei, X. Tetrahedron
Supporting information for this article is available online at
http://dx.doi.org/10.1055/s-0035-1562343.
(
S
u
p
p
ortioIgnfrm oaitn
S
u
p
p
ortioIgnfrm oaitn
2014, 70, 3854. (c) Fan, X.-H.; Yang, L.-M. Eur. J. Org. Chem. 2010,
References
2457.
(
16) Jezorek, R. L.; Zhang, N.; Leowanawat, P.; Bunner, M. H.;
Gutsche, N.; Pesti, A. K. R.; Olsen, J. T.; Percec, V. Org. Lett. 2014,
16, 6326.
(17) Malineni, J.; Jezorek, R. L.; Zhang, N.; Percec, V. Synthesis 2016,
48, in press; DOI: 10.1055/s-0035-1562342.
(18) (a) Gao, H.; Li, Y.; Zhou, Y.-G.; Han, F.-S.; Lin, Y.-J. Adv. Synth.
Catal. 2011, 353, 309. (b) Zhao, Y.-L.; Li, Y.; Li, S.-M.; Zhou, Y.-G.;
Sun, F.-Y.; Gao, L.-X.; Han, F.-S. Adv. Synth. Catal. 2011, 353, 1543.
(19) (a) Percec, V.; Bae, J. Y.; Zhao, M. Y.; Hill, D. H. J. Org. Chem. 1995,
60, 176. (b) Percec, V.; Okita, S.; Weiss, R. Macromolecules 1992,
25, 1816. (c) Percec, V.; Okita, S. J. Polym. Sci., Part A: Polym.
Chem. 1993, 31, 877. (d) Percec, V.; Okita, S. J. Polym. Sci., Part A:
Polym. Chem. 1993, 31, 1087. (e) Percec, V.; Bae, J. Y.; Zhao, M.
Y.; Hill, D. H. Macromolecules 1995, 28, 6726. (f) Grob, M. C.;
Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M. Y.; Hill, D. H.
Macromolecules 1996, 29, 7284. (g) Percec, V.; Zhao, M. Y.; Bae,
(
1) (a) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.;
Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111,
346. (b) Han, F.-S. Chem. Soc. Rev. 2013, 42, 5270.
1
(c) Mesganaw, T.; Garg, N. K. Org. Process Res. Dev. 2013, 17, 29.
(d) Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem. 2013, 19.
(e) Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43,
8081. (f) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014,
509, 299. (g) Su, B.; Cao, Z.-C.; Shi, Z.-J. Acc. Chem. Res. 2015, 48,
886. (h) Standley, E. A.; Tasker, S. Z.; Jensen, K. L.; Jamison, T. F.
Acc. Chem. Res. 2015, 48, 1503. (i) Tobisu, M.; Chatani, N. Acc.
Chem. Res. 2015, 48, 1717.
(2) Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J. Am.
Chem. Soc. 2009, 131, 17748.
(3) Antoft-Finch, A.; Blackburn, T.; Snieckus, V. J. Am. Chem. Soc.
2009, 131, 17750.
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Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–H