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Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides

Hofstra, Julie L. and Poremba, Kelsey E. and Shimozono, Alex M. and Reisman, Sarah E. (2019) Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides. Angewandte Chemie International Edition, 58 (42). pp. 14901-14905. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20190805-134105383

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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 H_2O 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.201906815DOIArticle
https://doi.org/10.26434/chemrxiv.8853056.v1DOIDiscussion Paper
ORCID:
AuthorORCID
Hofstra, Julie L.0000-0001-9558-4317
Poremba, Kelsey E.0000-0002-7446-257X
Reisman, Sarah E.0000-0001-8244-9300
Alternate Title:Ni-Catalyzed Conversion of Enol Triflates to Alkenyl Halides
Additional Information:© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: May 31, 2019; Revised manuscript received: August 9, 2019; Accepted manuscript online: August 13, 2019; Version of record online: September 19, 2019. We thank the following Caltech staff for their help: Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to experimental and analytical equipment; Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements; and Dr. Paul Oyala for assistance with EPR experiments. We also thank Jordan C. Beck for assistance in the preparation of alkenyl triflates 1 e and 1 k. Fellowship support was provided by the National Science Foundation (graduate research fellowship to J.L.H. and K.E.P., Grant No. DGE‐1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191‐01) is gratefully acknowledged. The authors declare no conflict of interest.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Heritage Medical Research InstituteUNSPECIFIED
NIHR35GM118191-01
Subject Keywords:nickel; halogenation; enol triflates; catalysis; alkenyl halides
Issue or Number:42
Record Number:CaltechAUTHORS:20190805-134105383
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20190805-134105383
Official Citation:J. L. Hofstra, K. E. Poremba, A. M. Shimozono, S. E. Reisman, Angew. Chem. Int. Ed. 2019, 58, 14901. https://doi.org/10.1002/anie.201906815
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:97642
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:05 Aug 2019 22:05
Last Modified:25 Jun 2021 19:00

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