A simple Lewis acid induced reaction of phenols with electrophiles: Synthesis of functionalized 4H-chromenes and ortho-benzylphenols

References

• (a) Hatakeyama, S.; Ochi, N.; Numata, H.; Takano, S. J. Chem. Soc. Chem. Comm. 1988, 17, 1202-1204. DOI: 10.1039/C39880001202.; (b) González, R.; Martín, N.; Seoane, C.; Marco, J.; Albert, A.; Cano, F. H. Tetrahedron Lett. 1992, 33, 3809-3812. DOI: 10.1016/0040-4039(92)80031-E.; (c) Wu, Y. C.; Liu, L.; Liu, Y. L.; Wang, D.; Chen, Y. J. J. Org. Chem. 2007, 72, 9383-9386. DOI: 10.1021/jo7015604.; (d) Thomas, N.; Zachariah, S. M. Asian J. Pharm. Clin. Res. 2013, 6, 11-15.; (e) Kjer, J.; Wray, V.; Edrada-Ebel, R.; Ebel, R.; Pretsch, A.; Lin, W.; Proksch, P. J. Nat. Prod. 2009, 72, 2053-2057. DOI: 10.1021/np900417g.
   Google Scholar
• (a) He, Y.; Hu, R.; Tong, R.; Li, F.; Shi, J.; Zhang, M. Molecules 2014, 19, 19253-19268. DOI: 10.3390/molecules191219253.; (b) Schmidt, T. J.; Khalid, S. A.; Romanha, A. J.; Alves, T. M. A.; Biavatti, M. W.; Brun, R.; Da Costa, F. B.; de Castro, S. L.; Ferreira, V. F.; de Lacerda, M. V. G.; et al. Curr. Med. Chem. 2012, 19, 2176-2228. DOI: 10.2174/092986712800229087.; (c) Wu, Y. C.; Li, H. J.; Liu, L.; Liu, Z.; Wang, D.; Chen, Y. J. Org. Biomol. Chem. 2011, 9, 2868-2877. DOI: 10.1039/c0ob01143f.; (d) Costa, M.; Dias, T. A.; Brito, A.; Proenca, F. Eur. J. Med. Chem. 2016, 123, 487-507. DOI: 10.1016/j.ejmech.2016.07.057.
   PubMed Web of Science ®Google Scholar
• (a) Raj, T.; Bhatia, R. K.; Kapur, A.; Sharma, M.; Saxena, A. K.; Ishar, M. P. S. Eur. J. Med. Chem. 2010, 45, 790-794. DOI: 10.1016/j.ejmech.2009.11.001.; (b) Mungra, D. C.; Patel, M. P.; Rajani, D. P.; Patel, R. G. Eur. J. Med. Chem. 2011, 46, 4192-4200. DOI: 10.1016/j.ejmech.2011.06.022.; (c) Aryapour, H.; Mahdavi, M.; Mohebbi, S. R.; Zali, M. R.; Foroumadi, A. Arch. Pharm. Res. 2012, 35, 1573-1582. DOI: 10.1007/s12272-012-0908-y.; (d) Conti, C.; Monaco, L. P.; Desideri, N. Bioorg. Med. Chem. 2014, 22, 1201-1207. DOI: 10.1016/j.bmc.2013.11.054.; (e) Mori, J.; Iwashima, M.; Takeuchi, M.; Saito, H. Chem. Pharm. Bull. 2006, 54, 391-396. DOI: 10.1248/cpb.54.391.; (f) He, X.; Chen, Y. Y.; Shi, J. B.; Tang, W. J.; Pan, Z. X.; Dong, Z. Q.; Song, B. A.; Li, J.; Liu, X. H. Bioorg. Med. Chem. 2014, 22, 3732-3738. DOI: 10.1016/j.bmc.2014.05.002.; (g) Johannes, C. W.; Visser, M. S.; Weatherhead, G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340-8347. DOI: 10.1021/ja981378o.
   PubMed Web of Science ®Google Scholar
• (a) Kandeel, M. M.; Kamal, A. M.; Abdelall, E. K.; Elshemy, H. A. J. Chem. Res. 2013, 37, 110-114. DOI: 10.3184/174751913X13573228322518.; (b) Das, S. G.; Hermanson, D. L.; Bleeker, N.; Lowman, X.; Li, Y.; Kelekar, A.; Xing, C. Acs Chem. Biol. 2013, 8, 327-335. DOI: 10.1021/cb300460f.
   Web of Science ®Google Scholar
• For 4H-chromenes from ketones, see: (a) Liu, Y.; Qian, J.; Lou, S.; Zhu, J.; Xu, Z. J. Org. Chem. 2010, 75, 1309-1312. DOI: 10.1021/jo902619x.;
   PubMed Web of Science ®Google Scholar
  (b) Xue, W. J.; Li, Q.; Gao, F. F.; Zhu, Y. P.; Wang, J. G.; Zhang, W.; Wu, A. X. ACS Comb. Sci. 2012, 14, 478-483. DOI: 10.1021/co3000506.;
   PubMed Web of Science ®Google Scholar
  (c) Li, H. J.; Deng, K.; Luo, D. H.; Liu, D. H.; Wang, J. L.; Lin, C. H.; Wu, Y. C. RSC Adv. 2014, 4, 26316-26324. DOI: 10.1039/C4RA03950E.;
   Web of Science ®Google Scholar
  (d) Pandey, K.; Choudhary, S.; Kumar, A. ChemistrySelect 2017, 2, 4452-4455. DOI: 10.1002/slct.201700928.;
   Web of Science ®Google Scholar
  (e) Deng, K.; Huai, Q. Y.; Li, H. J.; Wang, J. H.; Yang, H. R.; Liu, Y.; Wu, Y. C. Synthesis 2018, 50, 1482-1492. DOI: 10.1055/s-0036-1591021.;
   Web of Science ®Google Scholar
  (f) Qi, C.; Ramella, D.; Wensley, A. M.; Luan, Y. A. Adv. Synth. Catal. 2016, 358, 2604-2611. DOI: 10.1002/adsc.201600364.;
   Web of Science ®Google Scholar
  (g) Filimonov, S. I.; Savinsky, N. G.; Evstigneeva, E. M. Mendeleev Commun. 2003, 13, 194-197. DOI: 10.1070/MC2003v013n04ABEH001687.;
   Web of Science ®Google Scholar
  (h) Elderfield, R. C.; King, T. P. J. Am. Chem. Soc. 1954, 76, 5439-5445. DOI: 10.1021/ja01650a054.
   Web of Science ®Google Scholar
• For 4H-chromenes from alkynes, see: (a) Rao, V. K.; Kaswan, P.; Parang, K.; Kumar, A. Org. Biomol. Chem. 2015, 13, 11072-11077. DOI: 10.1039/C5OB01734C.;
   PubMed Web of Science ®Google Scholar
  (b) Moskalev, M. V.; Yakub, A. M.; Morozov, A. G.; Baranov, E. V.; Kazarina, O. V.; Fedushkin, I. L. Eur. J. Org. Chem. 2015, 2015, 5781-5788. DOI: 10.1002/ejoc.201500680.;
   Web of Science ®Google Scholar
  (c) Kinthada, L. K.; Babu, K. N.; Padhi, D.; Bisai, A. Eur. J. Org. Chem. 2017, 2017, 3078-3091. DOI: 10.1002/ejoc.201700507.
   Web of Science ®Google Scholar
• For naphthopyrans from propargylic alcohols, see: (a) Dong, Y. W.; Wang, G. W.; Wang, L. Tetrahedron 2008, 64, 10148-10154. DOI: 10.1016/j.tet.2008.08.047.;
   Web of Science ®Google Scholar
  (b) Pareek, A.; Dada, R.; Rana, M.; Sharma, A. K.; Yaragorla, S. RSC Adv. 2016, 6, 89732-89743. DOI: 10.1039/C6RA17411F.;
   Web of Science ®Google Scholar
  (c) Parker, K. A.; Mindt, T. L. Org. Lett. 2001, 3, 3875-3878. DOI: 10.1021/ol0167199.;
   PubMed Web of Science ®Google Scholar
  (d) Madabhushi, S.; Jillella, R.; Godala, K. R.; Mallu, K. K. R.; Beeram, C. R.; Chinthala, N. Tetrahedron Lett. 2012, 53, 5275-5279. DOI: 10.1016/j.tetlet.2012.07.077.;
   Web of Science ®Google Scholar
  (e) Yuan, F. Q.; Han, F. S. Adv. Synth. Catal. 2013, 355, 537-547. DOI: 10.1002/adsc.201200804.;
   Web of Science ®Google Scholar
  (f) Qiu, Y.-F.; Ye, Y.-Y.; Song, X.-R.; Zhu, X.-Y.; Yang, F.; Song, B.; Wang, J.; Hua, H.-L.; He, Y.-T.; Han, Y.-P.; et al. Chem. Eur. J. 2015, 21, 3480-3487. DOI: 10.1002/chem.201406100.;
   PubMed Web of Science ®Google Scholar
  (g) Xu, X.; Liu, J.; Liang, L.; Li, H.; Li, Y. Adv. Synth. Catal. 2009, 351, 2599-2604. DOI: 10.1002/adsc.200900483.;
   Web of Science ®Google Scholar
  (h) Pawar, G. G.; Tiwari, V. K.; Jena, H. S.; Kapur, M. Chem. Eur. J. 2015, 21, 9905-9911. DOI: 10.1002/chem.201500755.;
   PubMed Web of Science ®Google Scholar
  (i) Nishibayashi, Y.; Inada, Y.; Yoshikawa, M.; Hidai, M.; Uemura, S. Angew. Chem. Int. Ed. 2003, 42, 1495-1498. DOI: 10.1002/anie.200250532.
   PubMed Web of Science ®Google Scholar
• For chromenes from phenols with chalcone, see: (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Adv. Synth. Catal. 2007, 349, 1759-1764. DOI: 10.1002/adsc.200600622.;
   Web of Science ®Google Scholar
  (b) Fazeli, A.; Pflästerer, D.; Rudolph, M.; Hashmi, A. S. K. J. Organomet. Chem. 2015, 795, 68-70. DOI: 10.1016/j.jorganchem.2015.04.055.;
   Web of Science ®Google Scholar
  (c) Melen, R. L.; Wilkins, L. C.; Kariuki, B. M.; Wadepohl, H.; Gade, L. H.; Hashmi, A. S. K.; Stephan, D. W.; Hansmann, M. M. Organometallics 2015, 34, 4127-4137. DOI: 10.1021/acs.organomet.5b00546.;
   Web of Science ®Google Scholar
  (d) Hashmi, A. S. K.; Rudolph, M.; Bats, J. W.; Frey, W.; Rominger, F.; Oeser, T. Chem. Eur. J. 2008, 14, 6672-6678. DOI: 10.1002/chem.200800210.;
   PubMed Web of Science ®Google Scholar
  (e) Hashmi, A. S. K.; Wölfle, M.; Ata, F.; Hamzic, M.; Salathe, R.; Frey, W. Adv. Synth. Catal. 2006, 348, 2501-2508. DOI: 10.1002/adsc.200600367.
   Web of Science ®Google Scholar
• Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. Rev. 1999, 99, 723-744. DOI: 10.1021/cr980018g.
   PubMed Web of Science ®Google Scholar
• Wang, B. Coord. Chem. Rev. 2006, 250, 242-258. DOI: 10.1016/j.ccr.2005.05.012.
   Web of Science ®Google Scholar
• Alt, H. G.; Köppl, A. Chem. Rev. 2000, 100, 1205-1222. DOI: 10.1021/cr9804700.
   PubMed Web of Science ®Google Scholar
• For Lewis acid mediate reactions, see: (a) Sreenivasulu, C.; Reddy, A. G. K.; Satyanarayana, G. Org. Chem. Front. 2017, 4, 972-977. DOI: 10.1039/C6QO00531D.;
   Web of Science ®Google Scholar
  (b) Sreenivasulu, C.; Satyanarayana, G. Eur. J. Org. Chem. 2018, 2018, 2846-2857. DOI: 10.1002/ejoc.201800391.;
   Web of Science ®Google Scholar
  (c) Niharika, P.; Ramulu, B. V.; Satyanarayana, G. Org. Biomol. Chem. 2014, 12, 4347-4360. DOI: 10.1039/C4OB00490F.;
   PubMed Web of Science ®Google Scholar
  (d) Das, A.; Reddy, A. G. K.; Krishna, J.; Satyanarayana, G. RSC Adv. 2014, 4, 26662-26666. DOI: 10.1039/C4RA04763J;
   Web of Science ®Google Scholar
  (e) Ramulu, B. V.; Satyanarayana, G. RSC Adv. 2015, 5, 70972-70976. DOI: 10.1039/C5RA12234A.;
   Web of Science ®Google Scholar
  (f) Krishna, J.; Niharika, P.; Satyanarayana, G. RSC Adv. 2015, 5, 26749-26761. DOI: 10.1039/C5RA00955C.;
   Web of Science ®Google Scholar
  (g) Mahendar, L.; Satyanarayana, G. RSC Adv. 2016, 6, 20588-20597. DOI: 10.1039/C6RA03447K.
   Web of Science ®Google Scholar
• For chalcones from acetophenones, see: (a) Ott, A. A.; Goshey, C. S.; Topczewski, J. J. J. Am. Chem. Soc. 2017, 139, 7737-7740. DOI: 10.1021/jacs.7b04203.;
   PubMed Web of Science ®Google Scholar
  (b) Chaloner, P. A.; Hitchcock, P. B.; Langadianou, E.; Readey, M. J. Tetrahedron Lett. 1991, 32, 6037-6038. DOI: 10.1016/S0040-4039(00)79458-5.;
   Web of Science ®Google Scholar
  (c) Jiang, Q.; Jia, J.; Xu, B.; Zhao, A.; Guo, C. C. J. Org. Chem. 2015, 80, 3586-3596. DOI: 10.1021/acs.joc.5b00267.;
   PubMed Web of Science ®Google Scholar
  (d) Yoshitaka, O. J.; Takuwa, T.; Mukaiyama, T. Chemistry Lett. 2003, 32, 994-995.
   Web of Science ®Google Scholar
• For cyclotrimerization of ketones, see: (a) Tayebee, R.; Jarrahi, M.; Maleki, B.; Razi, M. K.; Mokhtari, Z. B.; Baghbanian, S. M. RSC Adv. 2015, 5, 10869-10877. DOI: 10.1039/C4RA11216D.;
   Web of Science ®Google Scholar
  (b) Xu, Y. L.; Pan, Y. M.; Wu, Q.; Wang, H. S.; Liu, P. Z. J. Org. Chem. 2011, 76, 8472-8476. DOI: 10.1021/jo201010d.
   PubMed Web of Science ®Google Scholar
• (a) Rueping, M.; Bootwicha, T.; Sugiono, E. Adv. Synth. Catal. 2010, 352, 2961-2965. DOI: 10.1002/adsc.201000538.;
   Web of Science ®Google Scholar
  (b) Wang, X.; Guram, A.; Caille, S.; Hu, J.; Preston, J. P.; Ronk, M.; Walker, S. Org. Lett. 2011, 13, 1881-1883. DOI: 10.1021/ol200422p.;
   PubMed Web of Science ®Google Scholar
  (c) Rueping, M.; Nachtsheim, B. J.; Scheidt, T. Org. Lett. 2006, 8, 3717-3719. DOI: 10.1021/ol0612962.;
   PubMed Web of Science ®Google Scholar
  (d) Gao, J.; Wang, J. Q.; Song, Q. W.; He, L. N. Green Chem. 2011, 13, 1182-1186. DOI: 10.1039/c1gc15056a.;
   Web of Science ®Google Scholar
  (e) Prades, A.; Corberán, R.; Poyatos, M.; Peris, E. Chem. Eur. J. 2009, 15, 4610-4613. DOI: 10.1002/chem.200802740.;
   PubMed Web of Science ®Google Scholar
  (f) Sun, G.; Sun, H.; Wang, Z.; Zhou, M. M. Synlett 2008, 2008, 1096-1100. DOI: 10.1055/s-2008-1042917.;
   Web of Science ®Google Scholar
  (g) Bering, L.; Jeyakumar, K.; Antonchick, A. P. Org. Lett. 2018, 20, 3911-3914. DOI: 10.1021/acs.orglett.8b01495.;
   PubMed Web of Science ®Google Scholar
  (h) Hosseinpour, R.; Pineda, A.; Garcia, A.; Romero, A. A.; Luque, R. J. Mol. Catal. A: Chem. 2015, 407, 32-37. DOI: 10.1016/j.molcata.2015.06.010.;
   Google Scholar
  (i) Pelzer, A. W.; Sturgeon, M. R.; Yanez, A. J.; Chupka, G.; O’Brien, M. H.; Katahira, R.; Cortright, R. D.; Woods, L.; Beckham, G. T.; Broadbelt, L. J. ACS Sustainable Chem. Eng. 2015, 3, 1339-1347. DOI: 10.1021/acssuschemeng.5b00070.;
   Web of Science ®Google Scholar
  (j) Wen, J.; Qi, H.; Kong, X.; Chen, L.; Yan, X. Synthetic Commun. 2014, 44, 1893-1903. DOI: 10.1080/00397911.2013.876547.;
   Web of Science ®Google Scholar
  (k) Fernández-Pérez, H.; Balakrishna, B.; Vidal-Ferran, A. Eur. J. Org. Chem. 2018, 2018, 1525-1532. DOI: 10.1002/ejoc.201701760.
   Web of Science ®Google Scholar
• (a) McCubbin, J. A.; Krokhin, O. V. Tetrahedron Lett. 2010, 51, 2447-2449. DOI: 10.1016/j.tetlet.2010.02.151.;
   Web of Science ®Google Scholar
  (b) Dada, R.; Singh, G.; Pareek, A.; Kausar, S.; Yaragorla, S. Tetrahedron Lett. 2016, 57, 3739-3742. DOI: 10.1016/j.tetlet.2016.07.010.;
   Web of Science ®Google Scholar
  (c) Sato, Y.; Aoyama, T.; Takido, T.; Kodomari, M. Tetrahedron 2012, 68, 7077-7081. DOI: 10.1016/j.tet.2012.06.063.;
   Web of Science ®Google Scholar
  (d) Suzuki, N.; Tsuchihashi, S.; Nakata, K. Tetrahedron Lett. 2016, 57, 1456-1459. DOI: 10.1016/j.tetlet.2016.02.064.;
   Web of Science ®Google Scholar
  (e) Yadav, J. S.; Bhunia, D. C.; Krishna, K. V.; Srihari, P. Tetrahedron Lett. 2007, 48, 8306-8310. DOI: 10.1016/j.tetlet.2007.09.140.;
   Web of Science ®Google Scholar
  (f) Srihari, P.; Bhunia, D. C.; Sreedhar, P.; Yadav, J. S. Synlett 2008, 2008, 1045-1049. DOI: 10.1055/s-2008-1072652.;
   Web of Science ®Google Scholar
  (g) Cullen, A.; Muller, A. J.; Williams, D. B. G. RSC Adv. 2017, 7, 42168-42171. DOI: 10.1039/C7RA08784E.
   Web of Science ®Google Scholar