Electrode

Organic chemistry

Combinatorial chemistry

Scope (computer science)

Olefin fiber

Engineering

Coupling (piping)

Catalysis

Nucleophile

Physical chemistry

Composite material

Chemistry

Materials science

Programming language

Ketone

Computer science

Reversing

Scalability

Electrochemistry

Database

Mechanical engineering

Journal of the American Chemical Society

A user-friendly approach is presented to sidestep the venerable Grignard addition to unactivated ketones to access tertiary alcohols by reversing the polarity of the disconnection. In this work a ketone instead acts as a nucleophile when adding to simple unactivated olefins to accomplish the same overall transformation. The scope of this coupling is broad as enabled using an electrochemical approach, and the reaction is scalable, chemoselective, and requires no precaution to exclude air or water. Multiple applications demonstrate the simplifying nature of the reaction on multistep synthesis, and mechanistic studies point to an intuitive mechanism reminiscent of other chemical reductants such as SmI2 (which cannot accomplish the same reaction).

Electroreductive Olefin–Ketone Coupling