Regio- and stereoselective functionalization of alkenes with emphasis on mechanistic insight and sustainability concerns

Abstract

Alkene is an attractive substrate for chemists due to its easy availability and reactivity towards large number of reactants affording diverse range of organic compounds. It reacts under ionic and free radical mechanisms including single electron transfer (SET). In this review, strategies used for C–C and C-heteroatom functionalization of alkene has been discussed with emphasis on the regio, stereoselectivity, mechanistic detail and sustainability aspects. These strategies mainly follow the free radical mechanism, and the highly reactive carbon radicals show uncontrollable regio- and stereoselectivities. Thus these strategies still need to be focused; especially in the asymmetric versions. The regio- and stereoselectivities of functionalization of alkenes have been highlighted and debated. In addition, the hazardous reagents such as Cl2, Br2 I2, CO, peroxides, and benzene have also been discussed with the emphasis on their impact on the environment. Their plausible green alternatives have also been suggested, such as MX as halogen replacement; CO surrogates (formaldehyde etc.); sustainable aromatic solvents as benzene replacement. The non-green strategies relying on pre-formed silyl hydride and their green alternative strategies such as transfer hydrogenations have also been indicated. The applications of the functionalization of alkenes for the total synthesis of bioactive compounds have also been discussed in detail. In addition, future perspectives are also highlighted for further developments in the functionalization of alkenes.

Keywords

• Regioselectivity
• Stereoselectivity
• Functionalization of Alkene
• Styrene