Alkenes are inexpensive, widely available feedstock and can be readily functionalized into complex organic molecules.[1] Owing to its omnipresence and unique reactivity, the functionalization of alkenes has become a powerful method for constructing complex organic molecules. Transition-metal-catalyzed functionalization of dormant C-H bonds has evolved as a robust synthetic methodology because it enables the synthesis of intricate organic motifs from the simple available substrates. In this context, direct olefinic C–H functionalization represents the ideal way of introducing an alkenyl group into organic molecules.[2] Transition-metal-catalyzed C–H functionalization of alkenes has gained special attention because it can construct complex carbon skeletons in a high regio- and stereoselective manner.[3] However, there are still limited examples of selective C–H functionalization of olefins, presumably due to the lability and increased reactivity relative to arenes. Realizing the need of a viable synthetic transformation for selective alkene functionalization, we have demonstrated selective C-H functionalization of acrylamides with unactivated alkenes to synthesize highly valuable substituted butadienes. [4a,b] Further, we also investigated the difference in selectivity between the cobalt and ruthenium using alkenyl acetates.[4c] On the other hand, we have also reported the synthesize of biologically important selenoflavones and oxindoles via Ru-catalyzed C-H functionalization of unsaturated carboxylic acids and amides. [4d,e]
References:
[1] Saini, V.; Stokes, B. J.; Sigman, M. S. Angew. Chem., Int. Ed. 2013, 52, 11206.
[2] Zhang, J.; Lu, X.; Shen, C.; Xu, L.; Ding, L.; Zhong, G. Chem. Soc. Rev, 2021, 50, 3263.
[3] Liu, B.; Yang, L.; Li, P.; Wang F.; Li, X. Org. Chem. Front. 2021, 8, 1085.
[4] (a) Logeswaran, R.; Jeganmohan, M. Org. lett. 2021, 23, 761-771. (b) Logeswaran, R.; Jeganmohan, M. Org. lett. 2023, 23, 6284-6289. (c) Logeswaran, R.; Jeganmohan, M. Org. lett. 2021, 23, 5679-5683. (d) Logeswaran, R.; Jeganmohan, M. J. Org. Chem. 2023, 88, 4554–4568. (e) Logeswaran, R.; Manoharan, R.; Jeganmohan, M. J. Org. Chem. 2019, 84, 14830-14843.