LOGIN TO YOUR ACCOUNT

Username
Password
Remember Me
Or use your Academic/Social account:

CREATE AN ACCOUNT

Or use your Academic/Social account:

Congratulations!

You have just completed your registration at OpenAire.

Before you can login to the site, you will need to activate your account. An e-mail will be sent to you with the proper instructions.

Important!

Please note that this site is currently undergoing Beta testing.
Any new content you create is not guaranteed to be present to the final version of the site upon release.

Thank you for your patience,
OpenAire Dev Team.

Close This Message

CREATE AN ACCOUNT

Name:
Username:
Password:
Verify Password:
E-mail:
Verify E-mail:
*All Fields Are Required.
Please Verify You Are Human:
fbtwitterlinkedinvimeoflicker grey 14rssslideshare1
Giorgi, Pascal D.; Miedziak, Peter John; Edwards, Jennifer Kelly; Hutchings, Graham John; Antoniotti, Sylvain (2017)
Publisher: Wiley
Languages: English
Types: Article
Subjects: QD
By combining nanocatalysis and base-catalysis, a novel one-pot multistep process was found for the synthesis of substituted heterocycles of biological relevance from simple substrates. It is based on an initial Au/O2 oxidation of allylic alcohols followed by a base-catalysed tandem hetero-Michael/aldolisation/crotonisation with ortho-hydroxy or ortho-amino benzaldehydes. The flexibility of the reaction even allowed the benzaldehyde partner to be prepared in situ in an example of one-pot/5-steps process.
  • The results below are discovered through our pilot algorithms. Let us know how we are doing!

    • [1] a) P. Anastas, J. Warner, Green chemistry: theory and practice, Oxford University Press, Oxford, 1998, 135. b) M. Poliakoff, P. Anastas, Nature 2001, 413, 257. c) R. A. Sheldon, Chem. Commun. 2008, 3352-3365. d) B. M. Trost, Science 1991, 254, 1471-1477.
    • [2] T. L. Lohr, T. J. Marks, Nat. Chem. 2015, 7, 477-482.
    • [3] a) X. Li, L. Yang, C. Peng, X. Xie, H.-J. Leng, B. Wang, Z.-W. Tang, G. He, L. Ouyang, W. Huang, B. Han, Chem. Commun. 2013, 49, 8692-8694. b) R. C. Wende, P. R. Schreiner, Green Chem. 2012, 14, 1821-1849.
    • [4] a) Y. Jeong, Y. Moon, S. Hong, Org. Lett. 2015, asap. b) L. Li, X.-H. Xia, Y. Wang, P. P. Bora, Q. Kang, Adv. Synth. Catal. 2015, 357, 2089-2097. c) Y. Oonishi, A. Gomez-Suarez, A. R. Martin, Y. Makida, A. M. Z. Slawin, S. P. Nolan, Chem. - Eur. J. 2014, 20, 13507-13510.
    • [5] C. A. Denard, M. J. Bartlett, Y. Wang, L. Lu, J. F. Hartwig, H. Zhao, ACS Catalysis 2015, 5, 3817-3822.
    • [6] B. Simmons, A. M. Walji, D. W. C. MacMillan, Angew. Chem. 2009, 121, 4413-4417; Angew. Chem. Int. Ed. 2009, 48, 4349-4353.
    • [7] a) G. He, F. Wu, W. Huang, R. Zhou, L. Ouyang, B. Han, Adv. Synth. Catal. 2014, 356, 2311-2319. b) C. B. Jacobsen, L. Albrecht, J. Udmark, K. A. Joergensen, Org. Lett. 2012, 14, 5526-5529. c) Y. Liu, M. Nappi, E. C. Escudero-Adan, P. Melchiorre, Org. Lett. 2012, 14, 1310-1313.
    • [8] D. Hager, D. W. C. MacMillan, J. Am. Chem. Soc. 2014, 136, 16986-16989.
    • [9] a) A. Noble, S. J. McCarver, D. W. C. MacMillan, J. Am. Chem. Soc. 2015, 137, 624-627. b) C. Vila, ChemCatChem 2015, 7, 1790-1793. c) L. Chu, J. M. Lipshultz, D. W. C. MacMillan, Angew. Chem. 2015, 127, 8040-8044; Angew. Chem. Int. Ed. 2015, 54, 7929-7933.
    • [10] K. Akagawa, S. Takigawa, E. Mano, K. Kudo, Tetrahedron Lett. 2011, 52, 770-773.
    • [11] N. Nelson, U. Chaudhary, K. Kandel, I. Slowing, Top. Catal. 2014, 57, 1000-1006.
    • [12] B. Sarmah, R. Srivastava, P. Manjunathan, G. V. Shanbhag, ACS Sustain. Chem. Eng. 2015, 3, 2933-2943.
    • [13] P. K. Sahoo, A. Bose, P. Mal, Eur. J. Org. Chem. 2015, 2015, 6994-6998.
    • [14] T. Yatabe, X. Jin, K. Yamaguchi, N. Mizuno, Angew. Chem. 2015, 127, 13500-13504; Angew. Chem. Int. Ed. 2015, 54, 13302-13306.
    • [15] X. Fang, R. Jackstell, A. Börner, M. Beller, Chem. Eur. J. 2014, 20, 15692-15696.
    • [16] a) K. A. Ostrowski, T. A. Faßbach, A. J. Vorholt, Adv. Synth. Catal. 2015, 357, 1374-1380. b) K. A. Ostrowski, T. A. Faßbach, D. Vogelsang, A. J. Vorholt, ChemCatChem 2015, 7, 2607-2613. c) K. Dong, R. Sang, J.-F. Soule, C. Bruneau, R. Franke, R. Jackstell, M. Beller, Chem. Eur. J. 2015, 21, 18033-18037.
    • [17] L. M. Ambrosini, T. A. Cernak, T. H. Lambert, Tetrahedron 2010, 66, 4882-4887.
    • [18] G. L. Brett, P. J. Miedziak, Q. He, D. W. Knight, J. K. Edwards, S. H. Taylor, C. J. Kiely, G. J. Hutchings, ChemSusChem 2013, 6, 1952-1958.
    • [19] a) L. L. Chng, J. Yang, J. Y. Ying, ChemSusChem 2015, 8, 1916-1925. b) H. Miyamura, H. Min, J.-F. Soulé, S. Kobayashi, Angew. Chem. Int. Ed. 2015, 54, 7564-7567. c) J.-F. Soulé, H. Miyamura, S. Kobayashi, Chem. Asian. J. 2013, 8, 2614-2626. d) G. T. Whiting, S. A. Kondrat, C. Hammond, N. Dimitratos, Q. He, D. J. Morgan, N. F. Dummer, J. K. Bartley, C. J. Kiely, S. H. Taylor, G. J. Hutchings, ACS Catalysis 2015, 5, 637-644.
    • [20] W.-J. Yoo, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 3095-3103.
    • [21] A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105; Angew. Chem. Int. Ed. 2006, 45, 7896-7936.
    • [22] E. Skupien, R. Berger, V. Santos, J. Gascon, M. Makkee, M. Kreutzer, P. Kooyman, J. Moulijn, F. Kapteijn, Catalysts 2014, 4, 89-115.
    • [23] H. Zou, R. Wang, J. Dai, Y. Wang, X. Wang, Z. Zhang, S. Qiu, Chem. Commun. 2015, 51, 14601-14604.
    • [24] D. I. Enache, J. K. Edwards, P. Landon, B. Solsona-Espriu, A. F. Carley, A. A. Herzing, M. Watanabe, C. J. Kiely, D. W. Knight, G. J. Hutchings, Science 2006, 311, 362-365.
    • [25] a) N. Dimitratos, J. A. Lopez-Sanchez, J. M. Anthonykutty, G. Brett, A. F. Carley, R. C. Tiruvalam, A. A. Herzing, C. J. Kiely, D. W. Knight, G. J. Hutchings, Phys. Chem. Chem. Phys. 2009, 11, 4952-4961. b) J. K. Edwards, B. E. Solsona, P. Landon, A. F. Carley, A. Herzing, C. J. Kiely, G. J. Hutchings, J. Catal. 2005, 236, 69-79.
    • [26] a) B. Lesch, J. Toröng, M. Nieger, S. Bräse, Synthesis 2005, 2005, 1888- 1900. b) N. Iwata, N. Wang, X. Yao, S. Kitanaka, J. Nat. Prod. 2004, 67, 1106-1109.
    • [27] Y. R. Lee, J. H. Choi, S. H. Yoon, Tetrahedron Lett. 2005, 46, 7539-7543.
    • [28] a) M. Menna, A. Aiello, F. D'Aniello, C. Imperatore, P. Luciano, R. Vitalone, C. Irace, R. Santamaria, Eur. J. Org. Chem. 2013, 2013, 3241-3246. b) Y. Noda, M. Yasuda, Helv. Chim. Acta 2012, 95, 1946-1952.
    • [29] J. H. Kim, N. Mahoney, K. L. Chan, R. J. Molyneux, B. C. Campbell, Cur. Microbiol. 2004, 49, 282-287.
    • [30] D. Harel, S. A. Khalid, M. Kaiser, R. Brun, B. Wünsch, T. J. Schmidt, J. Ethnopharmacol. 2011, 137, 620-625.
    • [31] M. Szczepanik, R. Obara, A. Szumny, B. Gabryś, A. Halarewicz-Pacan, J. Nawrot, C. Wawrzeńczyk, J. Agric. Food Chem. 2005, 53, 5905-5910.
    • [32] D. Lanari, O. Rosati, M. Curini, Tetrahedron Lett. 2014, 55, 1752-1755.
    • [33] M. C. Bröhmer, N. Volz, S. Bräse, Synlett 2009, 2009, 1383-1386.
    • [34] B. Sarmah, G. Baishya, N. Hazarika, P. J. Das, Synlett 2014, 26, 2151- 2155.
    • [35] a) T. Govender, L. Hojabri, F. M. Moghaddam, P. I. Arvidsson, Tetrahedron-Asymmetr. 2006, 17, 1763-1767. b) K. Liu, X. Jiang, Eur. J. Org. Chem. 2015, 2015, 6423-6428. c) H. Sundén, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J. 2007, 13, 574-581.
    • [36] a) K. Takenaka, Y. Tanigaki, M. L. Patil, C. V. L. Rao, S. Takizawa, T. Suzuki, H. Sasai, Tetrahedron-Asymmetr. 2010, 21, 767-770. b) M. Bobin, I. J. Day, S. M. Roe, E. M. E. Viseux, Dalton Trans. 2013, 42, 6592-6602.
    • [37] L. Calmus, A. Corbu, J. Cossy, Adv. Synth. Catal. 2015, 357, 1381-1386.
    • [38] X.-W. Du, L. M. Stanley, Org. Lett. 2015, 17, 3276-3279.
    • [39] D. Reinhard, L. Schöttner, V. Brosius, F. Rominger, M. Mastalerz, Eur. J. Org. Chem. 2015, 2015, 3274-3285.
    • [40] PCC: 0%; TEMPO/Cu: ~20%; AUROlite/O2: ~25% isolated yield of orthoaminobenzaldehyde
    • [41] S. Balieu, G. E. Hallett, M. Burns, T. Bootwicha, J. Studley, V. K. Aggarwal, J. Am. Chem. Soc. 2015, 137, 4398-4403.
  • No related research data.
  • No similar publications.

Share - Bookmark

Cite this article