Lu, Zhe and Wilsily, Ashraf and Fu, Gregory C. (2011) Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides. Journal of the American Chemical Society, 133 (21). pp. 8154-8157. ISSN 0002-7863. PMCID PMC3102136. doi:10.1021/ja203560q. https://resolver.caltech.edu/CaltechAUTHORS:20200428-095145872
![[img]](https://authors.library.caltech.edu/style/images/fileicons/application_pdf.png) |
PDF
- Accepted Version
See Usage Policy. 476kB |
|
PDF (Experimental procedures and compound characterization data)
- Supplemental Material
See Usage Policy. 943kB |
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20200428-095145872
Abstract
A new family of stereoconvergent cross-couplings of unactivated secondary alkyl electrophiles has been developed, specifically, arylamine-directed alkyl–alkyl Suzuki reactions. This represents the first such investigation to be focused on the use of alkyl chlorides as substrates. Structure–enantioselectivity studies are consistent with the nitrogen, not the aromatic ring, serving as the primary site of coordination of the arylamine to the catalyst. The rate law for this asymmetric cross-coupling is compatible with transmetalation being the turnover-limiting step of the catalytic cycle.
| Item Type: | Article | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Related URLs: |
| |||||||||
| ORCID: |
| |||||||||
| Additional Information: | © 2011 American Chemical Society. Received: April 18, 2011. Published: May 10, 2011. This study is dedicated to the memory of Prof. David Y. Gin. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871), Eli Lilly (fellowship to Z.L.), and the Martin Family Society of Fellows for Sustainability (fellowship to Z.L.). | |||||||||
| Funders: |
| |||||||||
| Subject Keywords: | Anions; Coupling reactions; Electrophiles'; Alkyls; Cross coupling reaction | |||||||||
| Issue or Number: | 21 | |||||||||
| PubMed Central ID: | PMC3102136 | |||||||||
| DOI: | 10.1021/ja203560q | |||||||||
| Record Number: | CaltechAUTHORS:20200428-095145872 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20200428-095145872 | |||||||||
| Official Citation: | Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides Zhe Lu, Ashraf Wilsily, and Gregory C. Fu Journal of the American Chemical Society 2011 133 (21), 8154-8157 DOI: 10.1021/ja203560q | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 102854 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | George Porter | |||||||||
| Deposited On: | 28 Apr 2020 19:07 | |||||||||
| Last Modified: | 16 Nov 2021 18:16 |
Repository Staff Only: item control page
