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Green Chemistry
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COMMUNICATION
Journal Name
DOI: 10.1039/C9GC02193K
Scheme 4 Proposed reaction mechanism.
unsaturated compounds were also found to be competent
substrates under our protocol. The reaction provides a novel
route to polysubstituted benzene rings under mild conditions
from cheap chemical feedstocks. Further studies are underway
to improve the method to obtain the heteroproduct (product
Conclusions
Overall, we have presented the preparation of polysubstituted
benzene compounds via benzannulation protocol in water
mediated by (NH4)2S2O8 from phenylacetylenes and α,β-
unsaturated compounds. The method is metal-free and allows
the preparation of unprecedented functionalized benzene
rings. Phenylacetylenes bearing different substituents were
suitable substrates in this transformation. Different α,β-
A
in Scheme 3) from styrene, phenylacetylenes and α,β-
unsaturated compounds according to the 3-component
reaction observed during the mechanistic studies.
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(a) D. Alberico, M. E. Scott and M. Lautens, Chem. Rev.,
2007, 107, 174; (b) Y. Yang, J. Lan and J. You, Chem. Rev.,
2017, 117, 8787; (c) C.-S. Wang, P. H. Dixneuf and J.-F. Soule,
Chem. Rev., 2018, 118, 7532; (d) S. R. Waldvogel, S. Lips, M.
Selt, B. Riehl and C. J. Kampf, Chem. Rev., 2018, 118, 6706.
Conflicts of interest
There are no conflicts to declare.
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5
V. Snieckus, Beilstein J. Org. Chem. 2011, 7, 1215 (and
references therein).
Acknowledgements
T. J. Colacot, New Trends in Cross-Coupling: Theory and
Applications, Royal Society of Chemistry, Cambridge, 2015.
H. J. Reich, Chem. Rev. 2013, 113, 7130.
We thank Fundação de Amparo à Pesquisa do Estado de São
Paulo (FAPESP, São Paulo, Brazil) for financial support (Grant
FAPESP 2017/18400-6). This study was financed in part by the
Coordenação de Aperfeiçoamento de Pessoal de Nível
Superior - Brasil (CAPES) - Finance Code 001.
6
7
(a) W. A. L. van Otterlo and C. B. de Koning, Chem. Rev.,
2009, 109, 3743; (b) P. Zhou, L. B. Huang, H. F. Jiang, A. Z.
Wang and X. W. Li, J. Org. Chem., 2010, 75, 8279; (c) W.
Song, S. A. Blaszczyk, J. Liu, S. Wang and W. Tang, Org.
Biomol. Chem., 2017, 15, 7490; (d) S. Li, X. X. Wu and S.
Chen, Org. Biomol. Chem. 2019, 17, 789.
8
9
(a) W.-M. Shu, K.-L. Zheng, J.-R. Ma and A.-X. Wu, Org. Lett.
2015, 17, 5216; (b) W.-M. Shu, K.-L. Zheng, J.-R. Ma and A.-X.
Wu, Org. Lett. 2016, 18, 3762; (c) S. M. B. Maezono, T. N.
Poudel, Y. Lee, Org. Biomol. Chem. 2017, 15, 2052; (d) F. Gao
and Y. Huang, Adv. Synth. Catal. 2014, 356, 2422; (e) L. Jiang,
H. Li, J. F. Zhou, M. W. Yuan, H. L. Li, Y. M. Chuan, M. L. Yuan,
Synth. Commun. 2018, 48, 336; (f) C. L. Zhang and S. Ye, Org.
Lett. 2016, 18, 6408; (g) M. Chang, C. Wu, J. Zheng, Y. Huang,
Chem. Asian J. 2016, 11, 1512.
Notes and references
1
(a) L. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. H. Gong and J. J.
Kido, Adv. Mater., 2011, 23, 926; (b) T. Kotipalli, V. Kavala, D.
Janreddy, C. Kuo, T. Kuo, H. Huang, C. He and C. Yao, RSC
Adv., 2014, 4, 2274; (c) T. Tomoo, T. Nakatsuka, T. Katayama,
Y. Hayashi, Y. Fujieda, M. Terakawa and K. Nagahira, J. Med.
Chem., 2014, 57, 7244; (d) P. Ruiz-Castillo and S. L. Buchwald,
Chem. Rev., 2016, 116, 12564.
(a) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz and M.
Lemaire, Chem. Rev., 2002, 102, 1359; (b) P. B. Arockiam, C.
Bruneau and P. H. Dixneuf, Chem. Rev., 2012, 112, 5879.
A. A. Greenfield, J. A. Butera and C. E. Caufield, Tetrahedron
Lett., 2003, 44, 2729 and references therein.
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4 | J. Name., 2012, 00, 1-3
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