Grubbs–Hoveyda Second-Generation Catalysts Activated by the Introduction of a Light Fluorous Tag onto the Bidentate Ligands

Abstract

Various novel Grubbs–Hoveyda second-generation catalysts activated by a fluorous tag on the ligands were prepared. The catalyst bearing the 1-naphthyl group on the bidentate ligand exhibited the highest catalytic activity among the studied catalysts for the ring-closing­-metathesis reaction of diethyl 2-allyl-2-(2-methylallyl)malonate.

Key words

catalyst - metathesis - ligands - fluorous - activation

• References

• 1a Fürstner A. Alkene Metathesis in Organic Synthesis . Springer; New York: 1998
• 1b Grubbs RH. Handbook of Metathesis . Wiley-VCH; Weinheim: 2003
• 1c Hoveyda AH, Malcolmson SJ, Meek SJ, Zhugralin AR. Angew. Chem. Int. Ed. 2010; 49: 34
• 1d Kong J, Chen C, Padros JB, Cao Y, Dunn RF, Dolman SJ, Janey J, Li H, Zacuto M. J. Org. Chem. 2012; 77: 3820
• 2 Kingsbury JS, Harrity PA, Bonitatebus PJ, Hoveyda AH. J. Am. Chem. Soc. 1999; 121: 791
• 3 Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168
• 4 Connon SJ, Blechert S. Angew. Chem. Int. Ed. 2003; 42: 1900
• 5 Matsugi M, Curran DP. J. Org. Chem. 2005; 70: 1636
• 6a Babunk M, Šimůnek O, Hosěk J, Rybáčková M, Cvačka J, Březinová A, Kvíčala J. J. Fluorine Chem. 2014; 161: 66
• 6b Tuba R, da Costa RC, Bazzi HS, Gladysz JA. ACS Catal. 2012; 2: 155
• 6c da Costa RC, Gladysz JA. Adv. Synth. Catal. 2007; 349: 243
• 6d da Costa RC, Gladysz JA. Chem. Commun. 2006; 2619
• 7 Matsugi M, Kobayashi Y, Suzumura N, Tsuchiya Y, Shioiri T. J. Org. Chem. 2010; 75: 7905
• 8a Love JA, Sanford MS, Day MW, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 10103
• 8b Trzaskowski B, Grela K. Organometallics 2013; 32: 3625
• 9a Curran DP. Separations with Fluorous Silica Gel and Related Materials . In Handbook of Fluorous Chemistry . Gladysz J, Horváth I, Curran DP. Wiley-VCH; Weinheim: 2004: 101
• 9b Curran DP, Hadida S, He M. J. Org. Chem. 1997; 62: 6714
• 9c Zhang W, Curran DP. Tetrahedron 2006; 62: 11837
• 10 Kobayashi Y, Inukai S, Kondo N, Watanabe T, Sugiyama Y, Hamamoto H, Shioiri T, Matsugi M. Tetrahedron Lett. 2015; 56: 1363
• 11a Zaja M, Connon SJ, Dunne AM, Rivard M, Buschmann N, Jiricek J, Blechert S. Tetrahedron 2003; 59: 6545
• 11b Wakamatsu H, Blechert S. Angew. Chem. Int. Ed. 2002; 41: 2403
• 11c Wakamatsu H, Blechert S. Angew. Chem. Int. Ed. 2002; 41: 794
• 12 Barbasiewicz M, Bieniek M, Michrowska A, Szadkowska A, Makal A, Woźniak K, Grela K. Adv. Synth. Catal. 2007; 349: 193
• 13 Matsugi M, Hasegawa M, Hasebe S, Takai S, Suyama R, Wakita Y, Kudo K, Imamura H, Hayashi T, Haga S. Tetrahedron Lett. 2008; 49: 4189
• 14 Kita Y, Sano A, Yamaguchi T, Oka M, Gotanda K, Murata K, Matsugi M. Org. Process Res. Dev. 1998; 2: 250
• 15a Kita Y, Sano A, Yamaguchi T, Oka M, Gotanda K, Matsugi M. Tetrahedron Lett. 1997; 38: 3549
• 15b Kita Y, Gotanda K, Sano A, Oka M, Murata K, Suemura M, Matsugi M. Tetrahedron Lett. 1997; 38: 8345
• 15c Kita Y, Sano A, Yamaguchi T, Oka M, Gotanda K, Matsugi M. J. Org. Chem. 1999; 64: 675
• 16a Wittig G, Schölkopf U. Chem. Ber. 1954; 87: 1318
• 16b Byrne PA, Gilheany DG. Chem. Soc. Rev. 2013; 42: 6670
• 17a Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
• 17b Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
• 18a Ullmann F, Bielecki J. Ber. Dtsch. Chem. Ges. 1901; 34: 2174
• 18b Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
• 19 Michrowska A, Mennecke K, Kunz U, Kirschning A, Grela K. J. Am. Chem. Soc. 2006; 128 13261
• 20 Kobayashi Y, Miyazaki H, Inukai S, Takagi C, Makino R, Shimowaki K, Igarashi R, Sugiyama Y, Nakamura S, Matsugi M. Synlett 2016; 27: 2352
• 21 Berlin JM, Campbell K, Ritter T, Funk TW, Chlenov A, Grubbs RH. Org. Lett. 2007; 9: 1339
• 22 Pozzi G, Cavazzini M, Cinato F, Montanari F, Quici S. Eur. J. Org. Chem. 1999; 1947