A new and highly effective organometallic approach to 1,2-dehalogenations and related reactions

We investigated the reductive elimination of several functionalized and non-functionalized vic-dibromides with 1,2-diphenyl-, 1,1,2,2-tetraphenyl- and 1-phenyl-2-(2-pyridyl)-1,2-disodioethane. The reaction, involving some of the less expensive organic and inorganic reagents, proceeds under mild conditions, and is tolerant of a variety of functional groups. Extension of this procedure to similar 1,2-disubstituted compounds was also investigated. Reductive eliminations run on stereochemical probe compounds strongly suggest that this reaction proceeds via a “single electron” reductive elimination reaction pathway.

We investigated the reductive elimination of several functionalized and non-functionalized vic-dibromides with 1,2-diaryl-1,2-disodiumethanes. The reaction proceeds under mild conditions, and is tolerant of a variety of functional groups. Extension of this procedure to similar 1,2-disubstituted-compounds was also investigated. Reductive eliminations run on stereochemical probe compounds strongly suggest that this reaction proceeds via a “single electron” reductive elimination reaction pathway.Figure optionsDownload as PowerPoint slide