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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 13
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SYNTHETIC COMMUNICATIONS REVIEWS

Heterogeneous gold(I)-catalyzed three-component reaction of aldehydes, alkynes, and orthoformates toward propargyl ethers

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Pages 1936-1945 | Received 09 Nov 2019, Published online: 18 May 2020

References

  • (a) Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim; 1995. (b) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373–381. DOI: 10.1021/ar990078o. (c) Negishi, E.-I.; Anastasia, L. Chem. Rev. 2003, 103, 1979–2017. DOI: 10.1021/cr020377i.
  • (a) Wakefield, B. J. Organolithium Methods; Academic: London, 1988; Chapter 3, p 32. (b) Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic; London, 1995; Chapter 3, pp 46–48.
  • Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245–11246. DOI: 10.1021/ja993074n.
  • (a) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363–1366. DOI: 10.1021/ol050069h. (b) Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760–13761. DOI: 10.1021/ja053946n. (c) Zhang, Y.; Li, P.; Wang, M.; Wang, L. J. Org. Chem. 2009, 74, 4364–4367. DOI: 10.1021/jo900507v.
  • (a) Wei, C.; Li, C.-J. Green Chem. 2002, 4, 39–41. DOI: 10.1039/b110102c. (b) Li, C.-J.; Wei, C. Chem. Commun. 2002, 2002, 268–269. DOI: 10.1039/b108851n.
  • Dhondi, P. K.; Chisholm, J. D. Org. Lett. 2006, 8, 67–69. DOI: 10.1021/ol0525260.
  • Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319–4321. DOI: 10.1021/ol017022q.
  • (a) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem. Int. Ed. 2002, 41, 2535–2538. DOI: 10.1002/1521-3773(20020715)41:14<2535::AID-ANIE2535>3.0.CO;2-M. (b) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem. Int. Ed. 2003, 42, 5763–5766. DOI: 10.1002/anie.200352578. (c) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638–5639. DOI: 10.1021/ja026007t. (d) Asano, Y.; Hara, K.; Ito, H.; Sawamura, M. Org. Lett. 2007, 9, 3901–3904. DOI: 10.1021/ol701534n. (e) Motoki, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 2997–3000. DOI: 10.1021/ol071003k. (f) Shi, L.; Tu, Y.-Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A. Org. Lett. 2004, 6, 1001–1003. DOI: 10.1021/ol049936t. (g) Choudary, B. M.; Sridhar, C.; Kantam, M. L.; Sreedhar, B. Tetrahedron Lett. 2004, 45, 7319–7321. DOI: 10.1016/j.tetlet.2004.08.004. (h) Kantam, M. L.; Yadav, J.; Laha, S.; Jha, S. Synlett. 2009, 2009, 1791–1794. DOI: 10.1055/s-0029-1217362.
  • Li, P.; Zhang, Y.; Wang, L. Chem. Eur. J. 2009, 15, 2045–2049. DOI: 10.1002/chem.200802643.
  • (a) Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395–4398. DOI: 10.1021/ol051575+. (b) Dodda, R.; Zhao, C.-G. Org. Lett. 2007, 9, 165–167. DOI: 10.1021/ol0627810. (c) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473–4475. DOI: 10.1021/ol035781y.
  • Li, P.; Wang, L. Chin. J. Chem. 2005, 23, 1076–1080.
  • (a) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584–9585. DOI: 10.1021/ja0359299. (b) Lo, V. K.-Y.; Liu, Y.; Wong, M.-K.; Che, C.-M. Org. Lett. 2006, 8, 1529–1532. DOI: 10.1021/ol0528641. (c) Huang, B.; Yao, X.; Li, C.-J. Adv. Synth. Catal. 2006, 348, 1528–1532. DOI: 10.1002/adsc.200606118. (d) Zhang, X.; Corma, A. Angew. Chem. Int. Ed. 2008, 47, 4358–4361. DOI: 10.1002/anie.200800098. (e) Layek, K.; Chakravarti, R.; Kantam, M. L.; Maheswaran, H.; Vinu, A. Green Chem. 2011, 13, 2878–2887. DOI: 10.1039/c1gc15518k. (f) Villaverde, G.; Corma, A.; Iglesias, M.; Sanchez, F. ACS Catal. 2012, 2, 399–406. DOI: 10.1021/cs200601w. (g) Price, G. A.; Brisdon, A. K.; Flower, K. R.; Pritchard, R. G.; Quayle, P. Tetrahedron Lett. 2014, 55, 151–154. DOI: 10.1016/j.tetlet.2013.10.141. (h) Price, G. A.; Brisdon, A. K.; Randall, S.; Lewis, E.; Whittaker, D. M.; Pritchard, R. G.; Muryn, C. A.; Flower, K. R.; Quayle, P. J. Organomet. Chem. 2017, 846, 251–262. DOI: 10.1016/j.jorganchem.2017.06.019. (i) Mariconda, A.; Sirignano, M.; Costabile, C.; Longo, P. Mol. Catal. 2020, 480, 110570. DOI: 10.1016/j.mcat.2019.110570. (j) Gholinejad, M.; Zareh, F.; Najera, C. Appl. Organometal. Chem. 2018, 32, e4454. DOI: 10.1002/aoc.4454. (k) Gholinejad, M.; Afrasi, M.; Najera, C. Appl. Organometal. Chem. 2019, 33, e4760. DOI: 10.1002/aoc.4760. (l) Gholinejad, M.; Bonyasi, R.; Najera, C.; Saadati, F.; Bahrami, M.; Dasvarz, N. ChemPlusChem. 2018, 83, 431–438. DOI: 10.1002/cplu.201800162.
  • (a) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem. Int. Ed. 2006, 45, 7896–7936. DOI: 10.1002/anie.200602454. (b) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180–3211. DOI: 10.1021/cr000436x. (c) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351–3378. DOI: 10.1021/cr068430g. (d) Wegner, H. A.; Auzias, M. Angew. Chem. Int. Ed. 2011, 50, 8236–8247. DOI: 10.1002/anie.201101603. (e) Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657–1712. DOI: 10.1021/cr100414u. (f) Dorel, R.; Echavarren, A. M. Chem. Rev. 2015, 115, 9028–9072. DOI: 10.1021/cr500691k. (g) Huple, D. B.; Ghorpade, S.; Liu, R. S. Adv. Synth. Catal. 2016, 358, 1348–1367. (h) Asiri, A. M.; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 4471–4503. DOI: 10.1039/C6CS00023A.
  • (a) Furstner, A. Chem. Soc. Rev 2009, 38, 3208–3221. (b) Cossy, J. Pure Appl. Chem. 2010, 82, 1365–1373. DOI: 10.1351/PAC-CON-09-09-12.
  • Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953–1955. DOI: 10.1021/ol060645p.
  • Xiao, F.; Chen, Y.; Liu, Y.; Wang, J. Tetrahedron. 2008, 64, 2755–2761. DOI: 10.1016/j.tet.2008.01.046.
  • (a) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414–8415. DOI: 10.1021/ja062777j. (b) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 14274–14275. DOI: 10.1021/ja066220f.
  • (a) Li, C.; Li, W.; Wang, J. Tetrahedron Lett. 2009, 50, 2536–2539. (b) Li, C.; Mo, F.; Li, W.; Wang, J. Tetrahedron Lett. 2009, 50, 6053–6056. DOI: 10.1016/j.tetlet.2009.08.049.
  • Kumar, M.; Jasinski, J.; Hammond, G. B.; Xu, B. Chem. Eur. J. 2014, 20, 3113–3119. DOI: 10.1002/chem.201304271.
  • (a) Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Chem. Rev. 2011, 111, 3036–3075. DOI: 10.1021/cr100230z. (b) Nasir Baig, R. B.; Varma, R. S. Chem. Commun. 2013, 49, 752–770. DOI: 10.1039/C2CC35663E. (c) Wang, D.; Astruc, D. Chem. Rev. 2014, 114, 6949–6985. DOI: 10.1021/cr500134h.
  • Yi, F.; Huang, B.; Nie, Q.; Cai, M. Tetrahedron Lett. 2016, 57, 4405–4410. DOI: 10.1016/j.tetlet.2016.08.062.
  • (a) Zhu, Y.; Sun, L.; Lu, P.; Wang, Y. ACS Catal. 2014, 4, 1911–1925. DOI: 10.1021/cs400922y. (b) Liang, T.; Zhang, W.; Chen, T.-Y.; Nguyen, K. D.; Krische, M. J. J. Am. Chem. Soc. 2015, 137, 13066–13071. DOI: 10.1021/jacs.5b08019. (c) Sogo, H.; Iwasawa, N. Angew. Chem. Int. Ed. 2016, 55, 10057–10060. DOI: 10.1002/anie.201604371. (d) Jimenez-Nunez, E.; Raducan, M.; Lauterbach, T.; Molawi, K.; Solorio, C. R.; Echavarren, A. M. Angew. Chem. Int. Ed. 2009, 48, 6152–6155. DOI: 10.1002/anie.200902248.
  • Nunez, A. J.; Shear, L. N.; Dahal, N.; Ibarra, I. A.; Yoon, J.; Hwang, Y. K.; Chang, J.-S.; Humphrey, S. M. Chem. Commun. 2011, 47, 11855–11857. DOI: 10.1039/c1cc14682c.

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