Alkyl halides as both hydride and alkyl sources in catalytic regioselective reductive olefin hydroalkylation

58Citations
Citations of this article
21Readers
Mendeley users who have this article in their library.
Get full text

Abstract

Among the plethora of catalytic methods developed for hydrocarbofunctionalization of olefins to date, reactions that regioselectively install a functionalized alkyl unit at the 2-position of a terminal unactivated C=C bond to afford branched products are scarce. Here, we show that a Ni-based catalyst in conjunction with a stoichiometric reducing agent promote Markovnikov-selective hydroalkylation of unactivated alkenes tethered to a recyclable 8-aminoquinaldine directing auxiliary. These mild reductive processes employ readily available primary and secondary haloalkanes as both the hydride and alkyl donor. Reactions of alkenyl amides with ≥ five-carbon chain length regioselectively afforded β-alkylated products through remote hydroalkylation, underscoring the fidelity of the catalytic process and the directing group’s capability in stabilizing five-membered nickelacycle intermediates. The operationally simple protocol exhibits exceptional functional group tolerance and is amenable to the synthesis of bioactive molecules as well as regioconvergent transformations.

Cite

CITATION STYLE

APA

Chen, X., Rao, W., Yang, T., & Koh, M. J. (2020). Alkyl halides as both hydride and alkyl sources in catalytic regioselective reductive olefin hydroalkylation. Nature Communications, 11(1). https://doi.org/10.1038/s41467-020-19717-6

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free