Abstract
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.
Supplementary materials
Title
Supplementary Materials
Description
The PDF file includes general experimental details, synthesis of ligands, typical procedure for arylative telomerization of isoprene, arylboron reagent scope, synthetic transformation of telomers, large-scale reaction, mechanistic study, copies of NMR spectra of products and supplementary references.
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