Nickel-catalyzed arylative telomerization of isoprene

Developing new transformations of bulky chemicals is an important approach to expand the reaction boundary of current chemistry. Instead of traditional hydroarylation of dienes, we herein demonstrate a nickel-catalyzed arylative telomerization of isoprene with high chemo- and regioselectivities. By utilizing a bulky mono-phosphine ligand, a range of structurally diverse aryl substituted terpenes are created efficiently under redox-neutral conditions. Preliminary mechanistic studies suggest this telomerization proceeds through an oxidative cyclometallation of isoprene with Ni(0) species followed by arylation with organoboron reagents. Beyond enabling efficient isoprene transformation, this work also provides a supplementary approach for the monoterpenoids synthesis.