Synthesis, Table of Contents Synthesis 2025; 57(05): 1043-1049DOI: 10.1055/a-2500-6556 paper Imidazo[1,5-a]pyridin-3-ylidene-Catalyzed Oxidative Esterification of Aldehydes: Remarkable Electronic Effect Regarding π-Accepting Character of Ring-Fused N-Heterocyclic Carbene Koki Endo , Fumitoshi Shibahara∗ Recommend Article Abstract Buy Article All articles of this category Abstract Imidazo[1,5-a]pyrid-3-ylidene (IPC)-catalyzed oxidative esterification of aldehydes was investigated. A series of IPCs showed good catalytic activity, in particular, sterically hindered ones. Substituents on the 3-position of imidazo[1,5-a]pyridine ring significantly influenced its catalytic activity, and electron-withdrawing substituent accelerated the reaction. Key words Key wordsNHC - esterification - substituent effect - imidazo[1,5-a]pyridine Full Text References References 1a Flanigan DM, Romanov-Michailidis F, White N, Rovis T. Chem. Rev. 2015; 115: 9307 1b Li Q, Zeng R, Han B, Li J. Chem. Eur. J. 2021; 27: 3238 2a Langdon SM, Wilde MD, Thai K, Gravel M. J. Am. Chem. Soc. 2014; 136: 7539 2b Stetter H. Angew. Chem. Int. Ed. 1976; 15: 639 2c Sarkar SD, Grimme S, Studer A. J. Am. Chem. Soc. 2010; 132: 1190 3 Ukai T, Tanaka R, Dokawa T. J. Pharm. Soc. Jpn. 1943; 63: 296 4 Breslow R. J. Am. Chem. Soc. 1958; 80: 3719 5 Risi CD, Brandolese A, Carmine GD, Ragno D, Massi A, Bortolini O. Chem. Eur. J. 2023; 29: e202202467 6a Alcarazo M, Roseblade SJ, Cowley AR, Fernández R, Brown JM, Lassaletta JM. J. Am. Chem. Soc. 2005; 127: 3290 6b Burstein C, Lehmann CW, Glorius F. Tetrahedron 2005; 61: 6207 7a Koto Y, Shibahara F, Murai T. Chem. Lett. 2016; 45: 1327 7b Koto Y, Shibahara F, Murai T. Org. Biomol. Chem. 2017; 15: 1810 8 Sarkar SD, Studer A. Org. Lett. 2010; 12: 1992 9 Hutt J, Aron Z. Org. Lett. 2011; 13: 5256 10 Huang P, Chen H. Chem. Commun. 2017; 53: 12584 11 Liu H, Eisen MS. Organometallics 2017; 36: 1461 12 Miao J, Fang P, Jagdeep S, Ge H. Org. Chem. Front. 2016; 3: 243 13 Cho EJ, Senecal TD, Kinzel T, Zhang Y, Watson DA, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 11628 14 Li Y, Du W, Deng W. Tetrahedron 2012; 68: 3611 15 Liu Q, Li G, He J, Liu J, Li P, Lei A. Angew. Chem. Int. Ed. 2010; 49: 3371 16 Zhang G, Irrgang T, Schlagbauer M, Kempe R. Chem. Catal. 2021; 1: 681 17 Tran BL, Fulton JL, Linehan JC, Lercher JA, Bullock RM. ACS Catal. 2018; 8: 8441 18 Wu X, Neumann H, Beller M. ChemCatChem 2010; 2: 509 19 Wu X, Neumann H, Beller M. Chem. Eur. J. 2012; 18: 3831 20 Liao W, Lin S, Kuo Y, Liang C. Org. Lett. 2022; 24: 4207 21 Isshiki R, Kurosawa M, Muto K, Yamaguchi J. J. Am. Chem. Soc. 2021; 143: 10333 22 Yasukawa T, Xi Y, Kobayashi S. Org. Lett. 2018; 20: 5172 23 Guo W, Lu L, Wang Y, Wang Y, Chem J, Xiao W. Angew. Chem. Int. Ed. 2015; 54: 2265 24 Tran UP. N, Oss G, Breugst M, Detmar E, Pace DP, Kevin L, Nguyen TV. ACS Catal. 2019; 9: 912 25 Zou H, Yang H, Liu Z, Mahmood MH, Mei G, Liu H, Chang C. Organometallics 2015; 34: 2791 26 Li Z, Wang C, Wang Y, Yuan D, Yao Y. Asian J. Org. Chem. 2018; 7: 810 27 Bantreil X, Kanfar N, Gehin N, Golliard E, Ohlmann P, Martinez J, Lamaty F. Tetrahedron 2014; 70: 5093 Supplementary Material Supplementary Material Supporting Information
