Published June 15, 2016
| Supplemental Material + Accepted Version
Journal Article
Open
Nickel-Catalyzed Intramolecular C−O Bond Formation: Synthesis of Cyclic Enol Ethers
- Creators
- Han, Seo-Jung
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Doi, Ryohei
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Stoltz, Brian M.
Abstract
An efficient and exceptionally mild intramolecular nickel-catalyzed carbon–oxygen bond-forming reaction between vinyl halides and primary, secondary, and tertiary alcohols has been achieved. Zinc powder was found to be an essential additive for obtaining high catalyst turnover and yields. This operationally simple method allows direct access to cyclic vinyl ethers in high yields in a single step.
Additional Information
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received 25 February 2016; version of record online 9 May 2016; issue online 15 June 2016. We wish to thank the NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. S.-J.H. thanks the Fulbright program (Foreign Student Program, No. 15111120) and the Ilju Foundation of Education & Culture (Pre-doctoral Research Fellowship) for financial support. R.D. is grateful for support as a JSPS research fellow. Dr. Mona Shahgholi (Caltech) and Naseem Torian (Caltech) are acknowledged for high-resolution mass spectrometry assistance. Dr. Scott C. Virgil (Caltech) is thanked for helpful discussions.Attached Files
Accepted Version - nihms805961.pdf
Supplemental Material - anie201601991-sup-0001-misc_information.pdf
Files
anie201601991-sup-0001-misc_information.pdf
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Additional details
- Alternative title
- Ni-Catalyzed Intramolecular C–O Bond Formation: Synthesis of Cyclic Enol Ethers
- PMCID
- PMC4985346
- Eprint ID
- 66937
- DOI
- 10.1002/anie.201601991
- Resolver ID
- CaltechAUTHORS:20160510-141655234
- R01GM080269-01
- NIH
- Amgen
- Gordon and Betty Moore Foundation
- Caltech Center for Catalysis and Chemical Synthesis
- 15111120
- Fulbright Foundation
- Ilju Foundation of Education & Culture
- Japan Society for the Promotion of Science (JSPS)
- Created
-
2016-05-11Created from EPrint's datestamp field
- Updated
-
2022-04-27Created from EPrint's last_modified field