This manuscript describes a visible-light-mediated organophotoredox catalytic process for vicinal difunctionalization of alkenes using heteroatom nucleophiles and aliphatic redox active esters. A wide range of heteroatom nucleophiles including alcohols, water, carboxylic acids, amides, and halogens can be used for this reaction. This radical relay type reaction allows forging of C(sp)-C(sp) with a carbon-centered radical and C(sp)-heteroatom bonds with a benzyl cation on the vinylarenes with complete regioselectivity in a single step.
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