K
M.-Y. Chang et al.
Paper
Synthesis
NMR (CDCl3) spectral data for all compounds and X-ray crystal struc-
(14) Desulfinative route toward the synthesis of stilbenes with Pd2+
:
ture analysis data of 6n, 6s, 7c, 7g and 8a are included.
S
u
p
p
o
nrtogI
f
rmoaitn
S
u
p
p
ortiInfogrmoaitn
For ArSO2H/styrenes, see: (a) Wang, G.-W.; Miao, T. Chem. Eur. J.
2011, 17, 5787. For ArSO2NHNH2/styrenes, see: (b) Yang, F.-L.;
Ma, X.-T.; Tian, S.-K. Chem. Eur. J. 2012, 18, 1582. For
ArSO2Na/styrenes, see: (c) Zhou, X.; Luo, J.; Liu, J.; Peng, S.;
Deng, G.-J. Org. Lett. 2011, 13, 1432.
References
(1) (a) Likhtenshtein, G. Stilbenes: Applications in Chemistry, Life
Sciences, and Materials Science; Wiley: New York, 2010. (b) Lo,
S.-C.; Burn, P. L. Chem. Rev. 2007, 107, 1097.
(2) (a) Roupe, K. A.; Remsberg, C. M.; Yanez, J. A.; Davies, N. M. Curr.
Clin. Pharmacol. 2006, 1, 81. (b) Baur, J. A.; Sinclair, D. A. Nat.
Rev. Drug Discov. 2006, 5, 493. (c) Cottart, C.-H.; Nivet-Antoine,
V.; Beaudeux, J.-L. Mol. Nutr. Food Res. 2014, 58, 7.
(3) (a) Cheng, L. T.; Tam, W.; Stevenson, S. H.; Meredith, G. R.;
Rikken, G.; Marder, S. R. J. Phys. Chem. 1991, 95, 10631.
(b) Soomro, S. A.; Benmouna, R.; Berger, R.; Meier, H. Eur. J. Org.
Chem. 2005, 3586. (c) Dorlars, A.; Schellhammer, C.-W.;
Schroeder, J. Angew. Chem., Int. Ed. Engl. 1975, 14, 665.
(d) Meier, H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1399.
(4) For selected examples on Julia–Kocienski olefination, see:
(a) Ghosh, A. K.; Zajc, B. J. Org. Chem. 2009, 74, 8531. (b) Aidhen,
I. S.; Mukkamala, R.; Weidner, C.; Sauer, S. Org. Lett. 2015, 17,
194.
(5) For selected examples on the Horner–Wadsworth–Emmons
reaction, see: (a) Molander, G. A.; Ham, J.; Canturk, B. Org. Lett.
2007, 7, 821. (b) Hilt, G.; Hengst, C. J. Org. Chem. 2007, 72, 7337.
(c) Ngwendson, J. N.; Atemnkeng, W. N.; Schultze, C. M.;
Banerjee, A. Org. Lett. 2006, 8, 4085.
(15) For reviews on desulfinative cross-coupling, see: (a) Aziz, J.;
Messaoudi, S.; Alami, M.; Hamze, A. Org. Biomol. Chem. 2014,
12, 9743. (b) Modha, S. G.; Mehta, V. P.; van der Eycken, E. V.
Chem. Soc. Rev. 2013, 42, 5042.
(16) Selected examples on the desulfinative carbonylation of car-
bonyl synthons, for nitriles/Pd2+
, see: (a) Behrends, M.;
Savmarker, J.; Sjoberg, P. J. R.; Larhed, M. ACS Catal. 2011, 1,
1455. (b) Liu, J.; Zhou, X.; Rao, H.; Xiao, F.; Li, C.-J.; Deng, G.-J.
Chem. Eur. J. 2011, 17, 7996. (c) Miao, T.; Wang, G.-W. Chem.
Commun. 2011, 47, 9501. For aldehydes/Rh+, see: (d) Rao, H.;
Yang, L.; Shuai, Q.; Li, C.-J. Adv. Synth. Catal. 2011, 353, 1701.
(17) For examples on desulfinative conjugation of enones, see:
(a) Wang, H.; Li, Y.; Zhang, R.; Jin, K.; Zhao, D.; Duan, C. J. Org.
Chem. 2012, 77, 4849. (b) Chen, W.; Zhou, X.; Xiao, F.; Luo, J.;
Deng, G.-J. Tetrahedron Lett. 2012, 53, 4347.
(18) For examples on direct desulfinative arylation of heterocycles
with Pd2+: For indoles, see: (a) Wu, M.; Luo, J.; Xiao, F.; Zhang,
S.; Deng, G.-J.; Luo, H.-A. Adv. Synth. Catal. 2012, 354, 335 For
xanthines, see. (b) Liu, B.; Guo, Q.; Cheng, Y.; Lan, J.; You, J.
Chem. Eur. J. 2011, 17, 13415. For thiazoles, benzoxazoles, and
benzothiazoles, see: (c) Chen, R.; Liu, S.; Liu, X.; Yang, L.; Deng,
G.-J. Org. Biomol. Chem. 2011, 9, 7675. For oxazoles, thiazoles,
and 1,3,4-oxadiazoles, see: (d) Wang, M.; Li, D.; Xhou, W.;
Wang, L. Tetrahedron 2012, 68, 1926. For benzothiophenes and
thiophenes, see: (e) Yuan, K.; Doucet, H. Chem. Sci. 2014, 5, 392.
For coumarins, see: (f) Jafarpour, F.; Olia, M. B. A.; Hazrati, H.
Adv. Synth. Catal. 2013, 355, 3407. For furans, see: (g) Beladhria,
A.; Yuan, K.; Ammar, H. B.; Soule, J. F.; Salem, R. B.; Doucet, H.
Synthesis 2014, 46, 2515. For benzo[d]oxazoles, see:
(h) Loukotova, L.; Yuan, K.; Doucet, H. ChemCatChem 2014, 6,
1303. For benzofurans, see: (i) Zhang, M.; Zhang, S.; Liu, M.;
Cheng, J. Chem. Commun. 2011, 47, 11522. For lactones, see:
(j) Li, J.; Yang, W.; Yang, S.; Huang, L.; Wu, W.; Sum, J.; Jiang, H.
Angew. Chem. Int. Ed. 2014, 53, 7219.
(19) (a) Liao, J.; Zhang, Z.; Tang, X.; Wu, W.; Guo, W.; Jiang, H. J. Org.
Chem. 2015, 80, 8903. (b) Yuan, K.; Soule, J.-F.; Doucet, H. ACS
Catal. 2015, 5, 978. (c) Skillinghaug, B.; Skold, C.; Rydfjord, J.;
Svensson, F.; Behrends, M.; Savmarker, J.; Sjoberg, P. J. R.;
Larhed, M. J. Org. Chem. 2014, 79, 12018. (d) Zhao, F.; Tan, Q.;
Xiao, F.; Zhang, S.; Deng, G.-J. Org. Lett. 2013, 15, 1520.
(e) Skillinghaug, B.; Rydfjord, J.; Odell, L. R. Tetrahedron Lett.
2016, 57, 533. (f) Ortgies, D. H.; Hassanpour, A.; Chen, F.; Woo,
S.; Forgione, P. Eur. J. Org. Chem. 2016, 408. (g) Sun, S.; Yu, J.-T.;
Jiang, Y.; Cheng, J. Adv. Synth. Catal. 2015, 357, 2022.
(20) (a) Ortgies, D. H.; Chen, F.; Forgione, P. Eur. J. Org. Chem. 2014,
3917. (b) Miao, T.; Wang, L. Adv. Synth. Catal. 2014, 356, 967.
(c) Miao, T.; Wang, L. Adv. Synth. Catal. 2014, 356, 429. (d) Xiao,
F.; Xie, H.; Liu, S.; Deng, G.-J. Adv. Synth. Catal. 2014, 356, 364.
(e) Chen, J.; Li, J.; Su, W. Org. Biomol. Chem. 2014, 12, 4078.
(f) Cheng, K.; Yu, H.-Z.; Zhao, B.; Hu, S.; Zhang, X.-M.; Qi, C. RSC
Adv. 2014, 4, 57923. (g) Li, J.; Bi, X.; Wang, H.; Xiao, J. RSC Adv.
2014, 4, 19214. (h) Aziz, J.; Messaoudi, S.; Alami, M.; Hamze, A.
Org. Biomol. Chem. 2014, 12, 9743. (i) Liu, S.; Tang, L.; Chen, H.;
Zhao, F.; Deng, G.-J. Org. Biomol. Chem. 2014, 12, 6076. (j) Miao,
T.; Li, P.; Wang, G.-W.; Wang, L. Chem. Asian J. 2013, 8, 3185.
(21) Chan, C.-K.; Huang, Y.-H.; Chang, M.-Y. Tetrahedron 2016, 72,
5521; and references cited therein.
(6) For selected examples on the Ramberg–Backlund rearrange-
ment, see: (a) Soderman, S. C.; Schwan, A. L. J. Org. Chem. 2012,
77, 10978. (b) Elizabeta, T. H.; Rozen, A. S. Org. Lett. 2006, 8,
1213.
(7) For selected examples on the McMurry coupling, see: (a) Xu, J.-
F.; Chen, Y.-Z.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Org. Lett. 2014,
16, 684. (b) Burhardt, M. N.; Ahlburg, A.; Skrydstrup, T. J. Org.
Chem. 2014, 79, 11830.
(8) For Pd2+-mediated cross-coupling of styrenes, see: (a) Allolio, C.;
Strassner, T. J. Org. Chem. 2014, 79, 12096. (b) Lu, G.-P.;
Voigtritter, K. R.; Cai, C.; Lipshutz, B. H. J. Org. Chem. 2012, 77,
3700. (c) Xu, H.-J.; Zhao, Y.-Q.; Zhou, X.-F. J. Org. Chem. 2011, 76,
8036. (d) McLaughlin, M. G.; McAdam, C. A.; Cook, M. J. Org. Lett.
2015, 17, 10. (e) Lasch, R.; Fehler, S. K.; Heinrich, M. R. Org. Lett.
2016, 18, 1586.
(9) For Co2+-mediated cross-coupling of styrenes, see: Moncomble,
A.; Le Floch, P.; Lledos, A.; Gosmini, C. J. Org. Chem. 2012, 77,
5056.
(10) For Ni2+-mediated cross-coupling of styrenes, see: Shimasaki,
T.; Konno, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2009, 11, 4890.
(11) For Rh3+-mediated cross-coupling of styrenes, see: (a) Mochida,
S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 3024.
(b) Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010,
12, 5776. (c) Patureau, F. W.; Nimphius, C.; Glorius, F. Org. Lett.
2011, 13, 6346.
(12) For Fe3+-mediated cross-coupling of styrenes, see: Heinrich, M.
R.; Blank, O.; Ullrich, D.; Kirschstein, M. J. Org. Chem. 2007, 72,
9609.
(13) For isomerization of stilbenes, see: (a) Saltiel, J. J. Am. Chem. Soc.
1967, 89, 1036. (b) Saltiel, J. J. Am. Chem. Soc. 1968, 90, 6394.
(c) Saltiel, J.; Waller, A. S.; Sears, D. F. Jr.; Garrett, C. Z. J. Phys.
Chem. 1993, 97, 2516. (d) Kim, I. S.; Dong, G. R.; Jung, Y. H. J. Org.
Chem. 2007, 72, 5424. (e) Parthasarathy, A.; Kaanumalle, L. S.;
Ramamurthy, V. Org. Lett. 2007, 9, 5059.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–L