DeLano, Travis J. and Reisman, Sarah E. (2019) Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis. ACS Catalysis, 9 (8). pp. 6751-6754. ISSN 2155-5435. PMCID PMC7190267. doi:10.1021/acscatal.9b01785. https://resolver.caltech.edu/CaltechAUTHORS:20190625-112222475
![[img]](https://authors.library.caltech.edu/style/images/fileicons/application_pdf.png) |
PDF
- Accepted Version
See Usage Policy. 457kB |
|
PDF (PubMed Central)
- Accepted Version
See Usage Policy. 932kB |
|
PDF (Experimental procedures and characterization data (1H and 13C NMR, HRMS, FTIR) for all new compounds)
- Supplemental Material
See Usage Policy. 5MB |
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20190625-112222475
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.
| Item Type: | Article | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Related URLs: |
| |||||||||
| ORCID: |
| |||||||||
| 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. | |||||||||
| Group: | Heritage Medical Research Institute | |||||||||
| Funders: |
| |||||||||
| Subject Keywords: | Nickel, electrochemistry, enantioselective, crosscoupling, asymmetric catalysis | |||||||||
| Issue or Number: | 8 | |||||||||
| PubMed Central ID: | PMC7190267 | |||||||||
| DOI: | 10.1021/acscatal.9b01785 | |||||||||
| Record Number: | CaltechAUTHORS:20190625-112222475 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20190625-112222475 | |||||||||
| Official Citation: | Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis. Travis J. DeLano and Sarah E. Reisman. ACS Catalysis 2019 9 (8), 6751-6754. DOI: 10.1021/acscatal.9b01785 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 96697 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 25 Jun 2019 18:29 | |||||||||
| Last Modified: | 15 Feb 2022 19:36 |
Repository Staff Only: item control page
