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. 2019 Oct 14;58(42):14901-14905.
doi: 10.1002/anie.201906815. Epub 2019 Sep 19.

Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides

Julie L Hofstra  1 , Kelsey E Poremba  1 , Alex M Shimozono  1 , Sarah E Reisman  1
Affiliations

Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides

Julie L Hofstra et al. Angew Chem Int Ed Engl. .

Abstract

A Ni-catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench-stable Ni(OAc)2 ⋅4 H2 O as a precatalyst and proceeds at room temperature in the presence of sub-stoichiometric Zn and either 1,5-cyclooctadiene or 4-(N,N-dimethylamino)pyridine.

Keywords: alkenes; halides; kinetics; nickel; reaction mechanisms.

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Figures

Scheme 1.
Scheme 1.
Synthesis and utility of alkenyl halides.
Scheme 2.
Scheme 2.
Mechanistic investigation.[a] [a] Reactions conducted under inert atmosphere on 0.2 mmol scale. [b] Determined by GC analysis versus undecane as an internal standard.
See this image and copyright information in PMC

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