Synthesis, Table of Contents Synthesis 2023; 55(21): 3575-3581DOI: 10.1055/a-2067-4041 special topic C–H Bond Functionalization of Heterocycles Decarboxylative Alkenylation of Imidazo[1,2-a]pyridines Using α,β-Unsaturated Carboxylic Acids via Pd-Catalyzed C–H Functionalization Authors Saurabh Kumar Neha Sharma Prabhakar Kaushal Kishor Krishna Nand Singh ∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract An efficient synthesis of alkenylated imidazo[1,2-a]pyridines has been accomplished using imidazo[1,2-a]pyridines and α,β-unsaturated carboxylic acids adopting C–H functionalization strategy in the presence of palladium acetate, 1,10-phenanthroline, and silver carbonate. Key words Key wordsalkenylation - C–H functionalization - C–C bond formation - decarboxylation - palladium Full Text References References 1a Davies HM. L, Morton D. J. Org. Chem. 2016; 81: 343 1b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147 1c Zhao B, Prabagar B, Shi Z. Chem 2021; 7: 2585 1d Chen K, Lei X. Curr. Opin. Green Sustain. Chem. 2018; 11: 9 1e Ranu BC, Ghosh T, Jalal S. ARKIVOK 2019; (iii): 79 2a Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976 2b McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885 2c Xing L, Luscombe CK. J. Mater. Chem. C 2021; 9: 16391 2d Singh K. Catalysts 2019; 9: 173 3a Enguehard-Gueiffier C, Gueiffier A. Med. Chem. 2007; 7: 888 3b Kishbaugh TL. S. Curr. Top. Med. Chem. 2016; 16: 3274 4a Goel R, Luxami V, Paul K. Curr. Top. Med. Chem. 2016; 16: 3590 4b Devi N, Singh D, Rawal RK, Bariwal J, Singh V. Curr. Top. Med. Chem. 2016; 16: 2963 5a Tashrifi Z, Mohammadi-Khanaposhtani M, Larijani B, Mahdavi M. Eur. J. Org. Chem. 2020; 269 5b Koubachi J, Kazzouli SE, Bousmina M, Guillaumet G. Eur. J. Org. Chem. 2014; 5119 5c Bagdi AK, Santra S, Monir K, Hajra A. Chem. Commun. 2015; 51: 1555 5d Konwar D, Bora U. ChemistrySelect 2021; 6: 2716 5e Berteina-Raboin S, Mouaddib A, Guillaumet G. Synthesis 2009; 271 5f Naas M, Kazzouli SE, Essassi EM, Bousmina M, Guillaumet G. Org. Lett. 2015; 17: 4320 6a McDonald RI, Liu G, Stahl SS. Chem. Rev. 2011; 111: 2981 6b Boyarskiy VP, Ryabukhin DS, Bokach NA, Vasilyev AV. Chem. Rev. 2016; 116: 5894 6c Chen S, Ranjan P, Voskressensky LG, Van der Eycken EV, Sharma UK. Molecules 2020; 25: 4970 6d Logeswaran R, Jeganmohan M. Adv. Synth. Catal. 2022; 364: 2113 6e Manoharan R, Jeganmohan M. Asian J. Org. Chem. 2019; 8: 1949 6f Pradhan S, De PB, Shah TA, Punniyamurthy T. Chem. Asian J. 2020; 15: 4184 6g Kumar SV, Banerjee S, Punniyamurthy T. Org. Chem. Front. 2020; 7: 1527 6h Panja S, Maity S, Majhi B, Ranu BC. Eur. J. Org. Chem. 2019; 5777 7a Beller M, Seayad J, Tillack A, Jiao H. Angew. Chem. Int. Ed. 2004; 43: 3368 7b Coombs John R, Morken JP. Angew. Chem. Int. Ed. 2016; 55: 2636 7c Zhou F, Li M, Jiang H, Wu W. Adv. Synth. Catal. 2021; 363: 4841 7d Goodall GW, Hayes W. Chem. Soc. Rev. 2006; 35: 280 7e Chen Z, Han X, Liang J.-H, Yin J, Yu G.-A, Liu S.-H. Chin. Chem. Lett. 2014; 25: 1535 7f Lin J, Song R.-J, Hu M, Li J.-H. Chem. Rec. 2019; 19: 440 7g Long J, Yuan Y, Shi Y. J. Am. Chem. Soc. 2003; 125: 13632 7h Crites CL, Hallet-Tapley GL, González-Béjar M, Netto-Ferreira JC, Scaiano JC. Chem. Commun. 2014; 50: 2289 7i Sihag P, Jeganmohan M. Synthesis 2021; 53: 3249 8a Zhang K, Bouakher AE, Levaique H, Bignon J, Retailleau P, Alami M, Hamze A. J. Org. Chem. 2019; 84: 13807 8b Ghosh M, Naskar A, Mitra S, Hajra A. Eur. J. Org. Chem. 2014; 715 9a Singh R, Allam BK, Singh N, Kumari KK, Singh SK, Singh KN. Org. Lett. 2015; 17: 2656 9b Kumar S, Singh R, Singh KN. Adv. Synth. Catal. 2018; 360: 422 9c Guntreddi T, Vanjari R, Singh KN. Org. Lett. 2015; 17: 976 9d Chand S, Sharma AK, Pandey AK, Singh KN. Org. Lett. 2022; 24: 6423 9e Chand S, Pandey AK, Singh KN. J. Org. Chem. 2021; 86: 6486 9f Guntreddi T, Vanjari R, Singh KN. Org. Lett. 2014; 16: 3624 10a Weaver JD, Recio AIII, Grenning AJ, Tunge JA. Chem. Rev. 2011; 111: 1846 10b Rodríguez N, Gooßen LJ. Chem. Soc. Rev. 2011; 40: 5030 10c Mehta VP, Van der Eycken EV. Chem. Soc. Rev. 2011; 40: 4925 10d Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215 10e Gooßen LJ, Rodriguez N, Gooßen K. Angew. Chem. Int. Ed. 2008; 47: 3100 11 Liu Y.-J, Xu H, Kong W.-J, Shang M, Dai H.-X, Yu J.-Q. Nature 2014; 515: 389 12 CCDC 2235835 (3j) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures 13 Mi X, Huang M, Zhang J, Wang C, Wu Y. Org. Lett. 2013; 15: 6266 14 Agasti S, Sharma U, Naveen T, Maiti D. Chem. Commun. 2015; 51: 5375 15 Wang C, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 4194 16 Kancherla R, Naveen T, Maiti D. Chem. Eur. J. 2015; 21: 8723 17 Tang J, Hackenberger D, Gooßen LJ. Angew. Chem. Int. Ed. 2016; 55: 11296 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)
