Nickel-Catalyzed Arylative Telomerization of Isoprene

Developing new transformations of bulk chemicals is an important approach to expand the reaction boundary of current chemistry. Instead of traditional hydroarylation of dienes, we herein demonstrated 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 was 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. This work not only offers a new transformation of isoprene, but also provides a complementary approach for the creation of unnatural monoterpenoids.