Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation

• DOI: 10.1126/science.aat2117
• Publication Date: 2018-10-03T08:49:24Z
• Authors: Timothy M. Monos; Rory C. McAtee; Corey R. J. Steph...
• Keywords: Alkene

Alkene aminoarylation with a single, bifunctional reagent is concise synthetic strategy. We report catalytic protocol for the addition of arylsulfonylacetamides across electron-rich alkenes complete anti-Markovnikov regioselectivity and excellent diastereoselectivity to provide 2,2-diarylethylamines. In this process, single-electron alkene oxidation enables carbon-nitrogen bond formation key benzylic radical poised Smiles-Truce 1,5-aryl shift. This reaction redox-neutral, exhibits broad functional group compatibility, occurs at room temperature loss sulfur dioxide. As process driven by visible light, uses readily available starting materials, demonstrates convergent synthesis, it well suited use in variety endeavors.