Synthesis, Inhaltsverzeichnis Synthesis 2021; 53(17): 3051-3056DOI: 10.1055/a-1477-7059 special topic Bond Activation – in Honor of Prof. Shinji Murai Iridium-Catalyzed Direct C–H Allylation of Ketimines Ryota Yabe a Department of Chemistry, Graduate School of Science, Osaka City University, Osaka 558-8585, Japan , Yusuke Ebe b Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan , Takahiro Nishimura ∗ a Department of Chemistry, Graduate School of Science, Osaka City University, Osaka 558-8585, Japan› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Aromatic C–H allylation of N-sulfonyl ketimines with allyl alcohol or allyl phenyl ether as an allyl source is catalyzed by a cationic iridium complex. The presence of a catalytic amount of a pyridine derivative was found to be essential for the reaction. In contrast, direct C–H allylation of ketimines derived from benzophenone derivatives and p-methoxyaniline with allyl phenyl ether proceeded in the absence of pyridine derivatives. Key words Key wordsallylation - iridium catalysis - imines - ketimines - C–H activation Volltext Referenzen References 1a Trost BM. Science 1991; 254: 1471 1b Trost BM. Angew. Chem. Int. Ed. 1995; 34: 259 2 For a recent review, see: Mishra NK, Sharma S, Park J, Han S, Kim IS. ACS Catal. 2017; 7: 2821 3a Oi S, Tanaka Y, Inoue Y. Organometallics 2006; 25: 4773 3b Kim M, Sharma S, Mishra NK, Han S, Park J, Kim M, Shin Y, Kwak JH, Han SH, Kim IS. Chem. Commun. 2014; 50: 11303 4a Achar TK, Zhang X, Mondal R, Shanavas MS, Maiti S, Maity S, Pal N, Paton RS, Maiti D. Angew. Chem. Int. Ed. 2019; 58: 10353 4b Bag SK. S, Mondal A, Jayarajan R, Dutta U, Porey S, Sunoj RB, Maiti D. J. Am. Chem. Soc. 2020; 142: 12453 5a Tsai AS, Brasse M, Bergman RG, Ellman JA. Org. Lett. 2011; 13: 540 5b Yu S, Li X. Org. Lett. 2014; 16: 1200 5c Mei S.-T, Wang N.-J, Ouyang Q, Wei Y. Chem. Commun. 2015; 51: 2980 6 Kuninobu Y, Ohta K, Takai K. Chem. Commun. 2011; 47: 10791 7 Zhang YJ, Skucas E, Krische MJ. Org. Lett. 2009; 11: 4248 8a Yu D.-G, Gensch T, de Azambuja F, Vasquez-Cespedes S, Glorius F. J. Am. Chem. Soc. 2014; 136: 17722 8b Gensch T, Vasquez-Cespedes S, Yu D.-G, Glorius F. Org. Lett. 2015; 17: 3714 9 Liu W, Richter SC, Zhang Y, Ackermann L. Angew. Chem. Int. Ed. 2016; 55: 7747 10a Cong X, Li Y, Wei Y, Zeng X. Org. Lett. 2014; 16: 3926 10b Aihara Y, Wuelbern J, Chatani N. Bull. Chem. Soc. Jpn. 2015; 88: 438 10c Barsu N, Kalsi D, Sundararaju B. Chem. Eur. J. 2015; 21: 9364 11a Asako S, Ilies L, Nakamura E. J. Am. Chem. Soc. 2013; 135: 17755 11b Asako S, Norinder J, Ilies L, Yoshikai N, Nakamura E. Adv. Synth. Catal. 2014; 356: 1481 12 Yao T, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2011; 50: 2990 13a Nishimura T, Ebe Y, Hayashi T. J. Am. Chem. Soc. 2013; 135: 2092 13b Nagamoto M, Nishimura T. Chem. Commun. 2014; 50: 6274 13c Ebe Y, Hatano M, Nishimura T. Adv. Synth. Catal. 2015; 357: 1425 14 Ebe Y, Nishimura T, Onoda M, Yorimitsu H. Angew. Chem. Int. Ed. 2017; 56: 5607 15 Simmons EM, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 3066 16 Herde JL, Lambert JC, Senoff CV. Inorg. Synth. 1974; 15: 18 17 Brookhart M, Grant B, Volpe AF. Jr. Organometallics 1992; 11: 3920 18 Nishimura T, Noishiki A, Tsui GC, Hayashi T. J. Am. Chem. Soc. 2012; 134: 5056 19 Xu B, Troian-Gautier L, Dykstra R, Martin RT, Gutierrez O, Tambar UK. J. Am. Chem. Soc. 2020; 142: 6206 20 Lahtigui O, Emmetiere F, Zhang W, Jirmo L, Toledo-Roy S, Hershberger JC, Macho JM, Grenning AJ. Angew. Chem. Int. Ed. 2016; 55: 15792 21 Cheemala MN, Knochel P. Org. Lett. 2007; 9: 3089 Zusatzmaterial Zusatzmaterial Supporting Information
