By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3′ position, the derived gold(I) complex possesses orthogonally positioned “push” and “pull” forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of &gt;26 p<i>K</i><sub>a</sub> units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions.

Soft propargylic deprotonation: Designed ligand enables Au-catalyzed isomerization of alkynes to 1,3-dienes

249th National Meeting (2015)

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