Published August 2, 2019
| Version Accepted Version + Supplemental Material
Journal Article
Open
Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis
Abstract
An electrochemically driven enantioselective nickel-catalyzed reductive cross-coupling of alkenyl bromides and benzyl chlorides is reported. The reaction forms products bearing allylic stereogenic centers with good enantioselectivity under mild conditions in an undivided cell. Electrochemical activation and turnover of the catalyst mitigate issues posed by metal powder reductants. This report demonstrates that enantioselective Ni-catalyzed cross-electrophile couplings can be driven electrochemically.
Additional Information
© 2019 American Chemical Society. Received: May 1, 2019; Revised: June 21, 2019; Published: June 25, 2019. We thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We thank Dr. Julie Hofstra for assistance with experimental design. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, T.J.D., 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 competing financial interest.Attached Files
Accepted Version - nihms-1039343.pdf
Supplemental Material - cs9b01785_si_001.pdf
Files
cs9b01785_si_001.pdf
Additional details
Identifiers
- PMCID
- PMC7190267
- Eprint ID
- 96697
- Resolver ID
- CaltechAUTHORS:20190625-112222475
Funding
- NSF Graduate Research Fellowship
- DGE-1144469
- Heritage Medical Research Institute
- NIH
- R35GM118191-01
Dates
- Created
-
2019-06-25Created from EPrint's datestamp field
- Updated
-
2022-02-15Created from EPrint's last_modified field
Caltech Custom Metadata
- Caltech groups
- Heritage Medical Research Institute