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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Copper-Catalyzed Cross-Coupling Between (E)-1,2-Diiodoethene and Carbazates: Entry to β-Functionalized N-Alkenylcarbazates

Author(s): Paméla Casault, Simon Ricard and Benoit Daoust*

Volume 19, Issue 9, 2022

Published on: 17 January, 2022

Page: [803 - 810] Pages: 8

DOI: 10.2174/1570180818666210803165347

Price: $65

Abstract

Aims: This work aims to widen the scope of methodologies to prepare functionalized N-alkenylcarbazates.

Background: Alkenylcarbazates are generally prepared via Aza-Baylis-Hillman reactions, nucleophilic attack on ketones or a tandem carbometallation/amidation reaction of alkynes.

Objective: The objective of this work is to develop a method to prepare functionalized Nalkenylcarbazates that alleviates the problem encountered in the above methods (use of electron deficient alkenes, use of stoiechiometric amounts of metal, access to symmetrical dicarbazates only).

Methods: Use of copper-catalyzed cross-coupling between vinylic diiodide and carbazates to prepare functionalized N-alkenylcarbazates.

Results: Various β-iodovinylcarbazates were synthesized with up to good yields. The highest yields were obtained using dicarbazates. Functionalization of β-iodovinylcarbazate demonstrated that the vinyl iodide moiety of these molecules can be substituted by a variety of functional groups via transition metal-catalyzed coupling reactions.

Conclusion: Copper-catalyzed cross-coupling reaction is efficient to prepare functionalized N-alkenylcarbazates.

Keywords: Cross-coupling, copper-catalyzed, carbazates, hydrazides, dihalogenoalkene, alkenylcarbazates, vinylation.

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[1]
Rivero, M.R.; Buchwald, S.L. Org. Lett., 2007, 9(6), 973-976.
[http://dx.doi.org/10.1021/ol062978s] [PMID: 17311390]
[2]
Zhou, C.; Ma, D. Chem. Commun. (Camb.), 2014, 50(23), 3085-3088.
[http://dx.doi.org/10.1039/c3cc49724k] [PMID: 24514455]
[3]
Martín, R.; Rodríguez Rivero, M.; Buchwald, S.L. Angew. Chem. Int. Ed., 2006, 45(42), 7079-7082.
[http://dx.doi.org/10.1002/anie.200602917]
[4]
Barluenga, J.; Gómez, N.; Palacios, F.; Gotor, V. Synthesis, 1981, 1981(07), 563-565.
[http://dx.doi.org/10.1055/s-1981-29530]
[5]
Palacios, F.; de Retana, A.M.; Oyarzabal, J.; Ezpeleta, J.M. Tetrahedron, 1998, 54(10), 2281-2288.
[http://dx.doi.org/10.1016/S0040-4020(97)10438-0]
[6]
Bezenšek, J.; Grošelj, U.; Stare, K.; Svete, J.; Stanovnik, B. Tetrahedron, 2012, 68(2), 516-522.
[http://dx.doi.org/10.1016/j.tet.2011.11.013]
[7]
Okitsu, T.; Kobayashi, K.; Kan, R.; Yoshida, Y.; Matsui, Y.; Wada, A. Org. Lett., 2017, 19(17), 4592-4595.
[http://dx.doi.org/10.1021/acs.orglett.7b02194] [PMID: 28809571]
[8]
Ferri, R.A.; Pitacco, G.; Valentin, E. Tetrahedron, 1978, 34(16), 2537-2543.
[http://dx.doi.org/10.1016/0040-4020(78)88384-7]
[9]
Mane, V.; Pandey, J.; Ayyagari, N.; Dey, C.; Kale, R.; Namboothiri, I.N.N. Org. Biomol. Chem., 2016, 14(8), 2427-2438.
[http://dx.doi.org/10.1039/C5OB02656C] [PMID: 26810956]
[10]
Kamimura, A.; Gunjigake, Y.; Mitsudera, H.; Yokoyama, S. Tetrahedron Lett., 1998, 39(40), 7323-7324.
[http://dx.doi.org/10.1016/S0040-4039(98)01570-6]
[11]
Shi, M.; Zhao, G-L. Tetrahedron, 2004, 60(9), 2083-2089.
[http://dx.doi.org/10.1016/j.tet.2003.12.059]
[12]
Dadwal, M.; Mobin, S.M.; Namboothiri, I.N.N. Org. Biomol. Chem., 2006, 4(13), 2525-2528.
[http://dx.doi.org/10.1039/B604899D] [PMID: 16791313]
[13]
Chen, X-Y.; Xia, F.; Ye, S. Org. Biomol. Chem., 2013, 11(34), 5722-5726.
[http://dx.doi.org/10.1039/c3ob40804c] [PMID: 23884292]
[14]
Otte, R.D.; Sakata, T.; Guzei, I.A.; Lee, D. Org. Lett., 2005, 7(3), 495-498.
[http://dx.doi.org/10.1021/ol0475008] [PMID: 15673273]
[15]
Zhang, Z-J.; Yi, D.; Fu, Q.; Liang, W.; Chen, S-Y.; Yang, L.; Du, F-T.; Ji, J-X.; Wei, W. Tetrahedron Lett., 2017, 58(25), 2417-2420.
[http://dx.doi.org/10.1016/j.tetlet.2017.05.005]
[16]
DeBergh, J.R.; Spivey, K.M.; Ready, J.M. J. Am. Chem. Soc., 2008, 130(25), 7828-7829.
[http://dx.doi.org/10.1021/ja803480b] [PMID: 18517202]
[17]
Nishimoto, Y.; Hirase, R.; Yasuda, M. Org. Lett., 2018, 20(12), 3651-3655.
[http://dx.doi.org/10.1021/acs.orglett.8b01371] [PMID: 29846079]
[18]
Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev., 2009, 109(1), 1-48.
[http://dx.doi.org/10.1021/cr068057c] [PMID: 19140772]
[19]
Kabalka, G.W.; Guchhait, S.K. Org. Lett., 2003, 5(22), 4129-4131.
[http://dx.doi.org/10.1021/ol035544v] [PMID: 14572266]
[20]
Wang, Z.; Skerlj, R.T.; Bridger, G.J. Tetrahedron Lett., 1999, 40(18), 3543-3546.
[http://dx.doi.org/10.1016/S0040-4039(99)00561-4]
[21]
Wolter, M.; Klapars, A.; Buchwald, S.L. Org. Lett., 2001, 3(23), 3803-3805.
[http://dx.doi.org/10.1021/ol0168216] [PMID: 11700143]
[22]
Jiang, L.; Lu, X.; Zhang, H.; Jiang, Y.; Ma, D. J. Org. Chem., 2009, 74(12), 4542-4546.
[http://dx.doi.org/10.1021/jo9006738] [PMID: 19432437]
[23]
Park, I-K.; Suh, S-E.; Lim, B-Y.; Cho, C-G. Org. Lett., 2009, 11(23), 5454-5456.
[http://dx.doi.org/10.1021/ol902250x] [PMID: 19886645]
[24]
Ma, F-F.; Peng, Z-Y.; Li, W-F.; Xie, X-M.; Zhang, Z. Synlett, 2011, 2011(17), 2555-2558.
[http://dx.doi.org/10.1055/s-0030-1260337]
[25]
Qian, Y.; Bolin, D.; Conde-Knape, K.; Gillespie, P.; Hayden, S.; Huang, K-S.; Olivier, A.R.; Sato, T.; Xiang, Q.; Yun, W.; Zhang, X. Bioorg. Med. Chem. Lett., 2013, 23(10), 2936-2940.
[http://dx.doi.org/10.1016/j.bmcl.2013.03.049] [PMID: 23582275]
[26]
Xu, L.; Peng, Y.; Pan, Q.; Jiang, Y.; Ma, D. J. Org. Chem., 2013, 78(7), 3400-3404.
[http://dx.doi.org/10.1021/jo400071h] [PMID: 23448680]
[27]
Yang, Z.; Hou, S.; He, W.; Cheng, B.; Jiao, P.; Xu, J. Tetrahedron, 2016, 72(17), 2186-2195.
[http://dx.doi.org/10.1016/j.tet.2016.03.019]
[28]
Barluenga, J.; Moriel, P.; Aznar, F.; Valdés, C. Org. Lett., 2007, 9(2), 275-278.
[http://dx.doi.org/10.1021/ol062726r] [PMID: 17217283]
[29]
Meyer, F.; Ueberschaar, N.; Dahse, H-M.; Hertweck, C. Bioorg. Med. Chem. Lett., 2013, 23(22), 6043-6045.
[http://dx.doi.org/10.1016/j.bmcl.2013.09.033] [PMID: 24113061]
[30]
Sanapo, G.F.; Daoust, B. Tetrahedron Lett., 2008, 49(26), 4196-4199.
[http://dx.doi.org/10.1016/j.tetlet.2008.03.157]
[31]
Ricard, S.; Gagnon, A.; Daoust, B. ChemistrySelect, 2018, 3(17), 4923-4929.
[http://dx.doi.org/10.1002/slct.201800824]
[32]
Ricard, S.; Ladouceur, F.; Couture, G.; Daoust, B. Heterocycles, 2020, 100(5)
[33]
Gilbert, N.; Ricard, S.; Bergeron, J.; Lambolez, P.; Daoust, B. Eur. J. Org. Chem., 2020, 5(17)
[34]
Kim, K-Y.; Shin, J-T.; Lee, K-S.; Cho, C-G. Tetrahedron Lett., 2004, 45(1), 117-120.
[http://dx.doi.org/10.1016/j.tetlet.2003.10.091]
[35]
Lam, M.S.; Lee, H.W.; Chan, A.S.C.; Kwong, F.Y. Tetrahedron Lett., 2008, 49(43), 6192-6194.
[http://dx.doi.org/10.1016/j.tetlet.2008.08.050]
[36]
Nilsson, J.; Gidlöf, R.; Nielsen, E.Ø.; Liljefors, T.; Nielsen, M.; Sterner, O. Bioorg. Med. Chem., 2011, 19(1), 111-121.
[http://dx.doi.org/10.1016/j.bmc.2010.11.050] [PMID: 21163663]
[37]
Park, J.; Kim, S-Y.; Kim, J-E.; Cho, C-G. Org. Lett., 2014, 16(1), 178-181.
[http://dx.doi.org/10.1021/ol4031638] [PMID: 24308811]
[38]
Beletskaya, I.P.; Cheprakov, A.V. Organometallics, 2012, 31(22), 7753-7808.
[http://dx.doi.org/10.1021/om300683c]
[39]
Beletskaya, I.P.; Cheprakov, A.V. Coord. Chem. Rev., 2004, 248(21), 2337-2364.
[http://dx.doi.org/10.1016/j.ccr.2004.09.014]
[40]
Sperotto, E.; van Klink, G.P.M.; van Koten, G.; de Vries, J.G. Dalton Trans., 2010, 39(43), 10338-10351.
[http://dx.doi.org/10.1039/c0dt00674b] [PMID: 21049595]
[41]
Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev., 2008, 108(8), 3054-3131.
[http://dx.doi.org/10.1021/cr8002505] [PMID: 18698737]
[42]
Chen, L.A.; Wang, C.F.; Lin, M.G.; Zhang, J.L.; Huang, P.Q. Asian J. Org. Chem., 2013, 2(4), 294-298.
[http://dx.doi.org/10.1002/ajoc.201300024]
[43]
Kim, J-Y.; Kim, D-H.; Jeon, T-H.; Kim, W-H.; Cho, C-G. Org. Lett., 2017, 19(17), 4688-4691.
[http://dx.doi.org/10.1021/acs.orglett.7b02372] [PMID: 28829140]
[44]
Ding, X.; Huang, M.; Yi, Z.; Du, D.; Zhu, X.; Wan, Y. J. Org. Chem., 2017, 82(10), 5416-5423.
[http://dx.doi.org/10.1021/acs.joc.7b00290] [PMID: 28436219]
[45]
Kim, M.H.; Kim, J. J. Org. Chem., 2018, 83(3), 1673-1679.
[http://dx.doi.org/10.1021/acs.joc.7b03119] [PMID: 29322782]
[46]
Zhang, J-Q.; Huang, G-B.; Weng, J.; Lu, G.; Chan, A.S.C. Org. Biomol. Chem., 2015, 13(7), 2055-2063.
[http://dx.doi.org/10.1039/C4OB02343A] [PMID: 25518836]
[47]
Zhang, J-Q.; Xiong, Y-S.; Chan, A.S.C.; Lu, G. RSC Advances, 2016, 6(88), 84587-84591.
[http://dx.doi.org/10.1039/C6RA13931K]
[48]
Zhang, J-Q.; Cao, J.; Li, W.; Li, S-M.; Li, Y-K.; Wang, J-T.; Tang, L. New J. Chem., 2017, 41(2), 437-441.
[http://dx.doi.org/10.1039/C6NJ03718F]
[49]
Xiong, X.; Jiang, Y.; Ma, D. Org. Lett., 2012, 14(10), 2552-2555.
[http://dx.doi.org/10.1021/ol300847v] [PMID: 22545771]
[50]
Takahashi, Y.; Miura, Y.; Yoshioka, N. New J. Chem., 2015, 39(6), 4783-4789.
[http://dx.doi.org/10.1039/C5NJ00393H]
[51]
Melkonyan, F.; Topolyan, A.; Yurovskaya, M.; Karchava, A. Eur. J. Org. Chem., 2008, 2008(35), 5952-5956.
[http://dx.doi.org/10.1002/ejoc.200800777]
[52]
Ball, P.; Nicholls, C.H. Dyes Pigm., 1982, 3(1), 5-26.
[http://dx.doi.org/10.1016/0143-7208(82)80010-7]
[53]
Kiewel, K.; Luo, Z.; Sulikowski, G.A. Org. Lett., 2005, 7(23), 5163-5165.
[http://dx.doi.org/10.1021/ol051993e] [PMID: 16268528]
[54]
Rao Maddali, L.N.; Jadhav Deepak, N.; Venkatesh, V. Eur. J. Org. Chem., 2009, 2009(25), 4300-4306.
[http://dx.doi.org/10.1002/ejoc.200900487]
[55]
Chacun-Lefèvre, L.; Bénéteau, V.; Joseph, B.T.; Mérour, J-Y. Tetrahedron, 2002, 58(51), 10181-10188.
[http://dx.doi.org/10.1016/S0040-4020(02)01404-7]
[56]
Montagne, C.; Laurent, N.; Joseph, B.; Mérour, J.Y. J. Heterocycl. Chem., 2009, 42(7), 1433-1441.
[http://dx.doi.org/10.1002/jhet.5570420728]

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