The construction of new C-C double bonds (olefination) is fundamentally important in organic chemistry and highly ubiquitous in the synthesis of materials and biologically relevant products. Many traditional olefination reactions, such as the Wittig, Julia, Peterson, Tebbe, Kauffmann and McMurry reactions, were carried out on carbonyl compounds as they are versatile organic precursors.[1] However, most of them use stoichiometric amounts of special reagents that pose issues with toxicity or product purification.[1] In this seminar, I would like to discuss our group adventure on the use of simple acid catalytic processes to promote interesting isodesmic reactions for the olefination of carbonyl compounds.[2-10]
[1] T. Takeda (ed.) “Modern Carbonyl Olefination: Methods and Applications”, Wiley, 2004.
[2] Tran, U. P. N.; Oss, G.; Pace, D. P.; Ho, J. and Nguyen T. V. Chem. Sci. 2018, 9, 5145-5151.
[3] Tran, U. P. N.; Oss, G.; Breugst, M.; Detmar, E. Pace, D. P.; Liyanto K. and Nguyen T. V.
ACS Catal. 2019, 9, 912-919.
[4] Oss, G. and Nguyen T. V. Synlett 2019, 30, 1966-1970.
[5] To, T. A.; Pei, C.; Koenigs, R. M. and Nguyen, T. V. Angew. Chem. Int. Ed. 2022, 61, e202117366.
[6] To, T. A.; Mai, K. B. and Nguyen, T. V. Org. Lett. 2022, 24, 7237-724.
[7] Mann, J. S.; Mai, K. B. and Nguyen, T. V. ACS Catal. 2023, 13, 2696-2701.
[8] Ho, T. H.; To, T. A.; Mai, K. B. and Nguyen, T. V. Org. Lett. 2024, 26, 8842-8847.
[9] To, T. A.; Phan, N. T. A.; Mai, K. B. and Nguyen, T. V. Chem. Sci. 2024, 15, 7187-7197.
[10] To, T. A. and Nguyen, T. V. Angew. Chem. Int. Ed. 2024, 63, e202317003.
[11] Ton, N. N. H.; Mai, B. K.; Fallon, T. and Nguyen, T. V. Angew. Chem. Int. Ed. 2025, 64, e202502713.