Published April 26, 2017
| Supplemental Material + Accepted Version
Journal Article
Open
Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes
Abstract
An asymmetric Ni-catalyzed reductive cross-coupling of (hetero)aryl iodides and benzylic chlorides has been developed to prepare enantioenriched 1,1-diarylalkanes. As part of these studies, a new chiral bioxazoline ligand, 4-heptyl-BiOX (L1), was developed in order to obtain products in synthetically useful yield and enantioselectivity. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, indoles, and piperidines.
Additional Information
© 2017 American Chemical Society. Received 17 February 2017. Published online 13 April 2017. We are grateful to Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We thank Dr. Leah Cleary for the initial preparation of ligands and Julie Hofstra for solving the structure of 3k (CCDC Deposition No. 1533022). Fellowship support was provided by the National Science Foundation (graduate research fellowship to K. E. P., Grant No. DGE-1144469), Amgen (Graduate Research Fellowship to N.T.K.), and Shionogi & Co., Ltd. (fellowship to N.S.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (NIGMS R35GM118191-01; GM111805-01) is gratefully acknowledged.Attached Files
Accepted Version - jacs.8b05247.pdf
Accepted Version - nihms948139.pdf
Supplemental Material - ja7b01705_si_001.cif
Supplemental Material - ja7b01705_si_002.pdf
Supplemental Material - ja7b01705_si_003.pdf
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Additional details
- PMCID
- PMC5851002
- Eprint ID
- 76561
- Resolver ID
- CaltechAUTHORS:20170414-064225830
- DGE-1144469
- NSF Graduate Research Fellowship
- Amgen
- Shionogi & Co., Ltd.
- American Cancer Society
- Heritage Medical Research Institute
- R35GM118191-1
- NIH
- GM111805-01
- NIH
- Created
-
2017-04-14Created from EPrint's datestamp field
- Updated
-
2022-03-28Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute