Ir(III)-Catalyzed Stereoselective Haloamidation of Alkynes Enabled by Ligand Participation

Seung Youn Hong; Junsoo Son; Dongwook Kim; Sukbok Chang

doi:10.1021/jacs.8b08134

Ir(III)-Catalyzed Stereoselective Haloamidation of Alkynes Enabled by Ligand Participation

J Am Chem Soc. 2018 Oct 3;140(39):12359-12363. doi: 10.1021/jacs.8b08134. Epub 2018 Sep 21.

Authors

Seung Youn Hong^{1

2}, Junsoo Son^{1

2}, Dongwook Kim^{1

2}, Sukbok Chang^{1

2}

Affiliations

¹ Department of Chemistry , Korea Advanced Institute of Science and Technology , Daejeon 34141 , Korea.
² Center for Catalytic Hydrocarbon Functionalizations , Institute for Basic Science , Daejeon 34141 , Korea.

PMID: 30217108
DOI: 10.1021/jacs.8b08134

Abstract

Described herein is the application of a strategy of ligand participation for the Ir-catalyzed imido transfer into alkynes. On the basis of a stoichiometric [3 + 2] cycloaddition of Cp*Ir(III)(κ²- N, O-chelate) with alkynyl dioxazolone, a catalytic haloamidation was developed for the first time by employing [Cp*IrCl₂]₂ precatalyst and NaX salts (X = Cl or Br) as practical halide sources to furnish synthetically versatile Z-(halovinyl)lactams with excellent stereoselectivity.

Publication types

Research Support, Non-U.S. Gov't