Research / 2020 / Article / Fig 1

Research Article

Selective Dealkenylative Functionalization of Styrenes via C-C Bond Cleavage

Figure 1

Functionalization based on styrenes. (a) Typical representative transformation patterns of styrene derivatives: C(sp2)-H activation (for example, Heck-type reaction), C(allylic)-H activation, and C=C double bond activation (for example, wacker oxidation, difunctionalization, polymerization, and metathesis). However, other activation mode is still undeveloped yet very desired to synthetic chemistry. (b) Long-standing unmet challenges in the field of carbon-carbon bond cleavage chemistry of styrenes: although the C=C bond cleavage has been well studied, the dealkenylative C(Ar)-C(alkenyl) single bond cleavage is still unknown. (c) The proposed cascade activation strategy whereby the initial C=C double bond preactivation and the consecutive C(Ar)-C1 single bond cleavage sequence may provide a chance to address the above unsolved dealkenylative transformation. However, the C1-C2 single bond cleavage in conventional styrene chemistry would be a challenging competitive path of the desired process. (d) This work: dealkenylative C-C bond amination and hydroxylation. FG: functional group.