Published October 14, 2019
| Accepted Version + Supplemental Material + Submitted
Journal Article
Open
Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides
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.
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.Attached Files
Accepted Version - nihms-1046681.pdf
Submitted - 2019-5-22-JLH_KEP_AMS_SER_Final_Preprint.pdf
Supplemental Material - anie201906815-s1-2019-8-9_jlh_kep_ams_supportinginformation_accepted.pdf
Files
anie201906815-s1-2019-8-9_jlh_kep_ams_supportinginformation_accepted.pdf
Additional details
- Alternative title
- Ni-Catalyzed Conversion of Enol Triflates to Alkenyl Halides
- PMCID
- PMC7179072
- Eprint ID
- 97642
- Resolver ID
- CaltechAUTHORS:20190805-134105383
- DGE-1144469
- NSF Graduate Research Fellowship
- Heritage Medical Research Institute
- R35GM118191-01
- NIH
- Created
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2019-08-05Created from EPrint's datestamp field
- Updated
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2023-03-24Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute