Migratory allylic arylation of 1,n-enols enabled by nickel catalysis.

ABSTRACT: Transition-metal-catalyzed allylic substitution reactions (Tsuji-Trost reactions) proceeding via a π-allyl metal intermediate have been demonstrated as a powerful tool in synthetic chemistry. Herein, we disclose an unprecedented π-allyl metal species migration, walking on the carbon chain involving 1,4-hydride shift as confirmed by deuterium labeling experiments. This migratory allylic arylation can be realized under dual catalysis of nickel and lanthanide triflate, a Lewis acid. Olefin migration has been observed to preferentially occur with the substrate of 1,n-enols (n ≥ 3). The robust nature of the allylic substitution strategy is reflected by a broad scope of substrates with the control of regio- and stereoselectivity. DFT studies suggest that π-allyl metal species migration consists

SUBMITTER: Zhao D 

PROVIDER: S-EPMC10247813 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature