Olefins as Unprecedented Feedstock for the Synthesis of Valuable Heterocycles: Regioselectivity Remains an Issue

Abstract

In the current time, the development of new synthetic strategies, capable of enabling step efficiency and atom economy by utilizing easily accessible starting materials is highly desirable. In this regard, the C–H activation protocol is one of the most promising approaches. The synthesis of heterocyclic moieties via a C–H activation protocol starting from easy-to-handle, readily accessible starting materials is extremely important and desirable. Olefins are generally considered as chemical feedstock for the synthesis of various valuable products due to their wide availability. Although unactivated olefins are easy to handle, due to their unbiased nature achieving total regioselectivity remains a challenge.

Key words

olefin - heterocycle - C–H activation - transition metal

• References

• 1a Zhang H, Qiu S, Tamez P, Tan GT, Aydogmus Z, Hung NV, Cuong NM, Angerhofer C, Soejarto DD, Pezzuto JM, Fong HH. S. Pharm. Biol. 2002; 40: 221
• 1b Sato H, Kawagishi H, Nishimura T, Yoneyama S, Yoshimoto Y, Sakamura S, Furusaki A, Katsuragi S, Matsumoto T. Agric. Biol. Chem. 1985; 49: 2969
• 2a Shan D, Gao Y, Jia Y. Angew. Chem. Int. Ed. 2013; 52: 4902
• 2b Guo L, Zhang F, Hu W, Lia L, Jia Y. Chem. Commun. 2014; 50: 3299
• 3 Reichard HA, Micalizio GC. Chem. Sci. 2011; 2: 573
• 4a Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011; 133: 6449
• 4b Rakhsit S, Grohmann C, Besset T, Glorius F. J. Am. Chem. Soc. 2011; 133: 2350
• 4c Hartwig J. Organotransition Metal Chemistry: From Bonding to Catalysis, 2010
• 5 Hyster TK, Dalton DM, Rovis T. Chem. Sci. 2015; 6 in press; DOI: 10.1039/C4SC02590C
• 6 Huckins JR, Bercot EA, Thiel OR, Hwang TL, Bio MM. J. Am. Chem. Soc. 2013; 135: 14492
• 7 Neely JM, Rovis T. J. Am. Chem. Soc. 2013; 135: 66
• 8a Sharma U, Tagoti N, Maji A, Manna S, Maiti D. Angew. Chem. Int. Ed. 2013; 52: 12669
• 8b Sharma U, Kancherla R, Tagoti N, Agasti S, Maiti D. Angew Chem. Int. Ed. 2014; 53: 11895