Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis. Academic Article uri icon

abstract

  • Herein, the introduction of oxa- and azabenzonorbornadienes into photoredox/nickel dual catalysis in a regioselective and diastereoselective transformation is disclosed. The inherent advantages of this dual catalytic system allow the use of alkyl motifs forming exclusively cis-1,2-dihydro-1-naphthyl alcohol backbones using readily accessible 4-alkyl-1,4-dihydropyridines (DHPs). Whereas previous studies have emphasized the use of nucleophilic organometallic coupling partners, this protocol grants access to a rather unexplored core featuring alkyl residues, while avoiding the use of highly reactive organometallic species (i.e., M = Al, Mg, Li, Zn, Zr). DFT calculations support a oxidative addition/reductive elimination mechanism, followed by a Curtin-Hammett scenario that controls the regioselectivity of the process, unlike previously reported transformations that proceed via a carbometalation/ -oxygen elimination mechanism.

published proceedings

  • ACS Catal

altmetric score

  • 2.5

author list (cited authors)

  • Luo, Y., Gutirrez-Bonet, . ., Matsui, J. K., Rotella, M. E., Dykstra, R., Gutierrez, O., & Molander, G. A.

citation count

  • 27

complete list of authors

  • Luo, Youran||Gutiérrez-Bonet, Álvaro||Matsui, Jennifer K||Rotella, Madeline E||Dykstra, Ryan||Gutierrez, Osvaldo||Molander, Gary A

publication date

  • January 2019