Published September 17, 2010
| Supplemental Material + Accepted Version
Journal Article
Open
Room-Temperature Alternative to the Arbuzov Reaction: The Reductive Deoxygenation of Acyl Phosphonates
Abstract
The reductive deoxygenation of acyl phosphonates using a Wolff−Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.
Additional Information
© 2010 American Chemical Society. Received July 6, 2010. Publication Date (Web): August 20, 2010. We gratefully acknowledge the Caltech Center for Catalysis and Chemical Synthesis for screening and its director Dr. Scott Virgil for helpful discussions. This work was supported by the NIH (NS 34407) and an NIH training grant for S.K. (NRSA 5-T32-GM07616).Attached Files
Accepted Version - nihms-231071.pdf
Supplemental Material - ol1015493_si_001.pdf
Files
nihms-231071.pdf
Files
(1.7 MB)
| Name | Size | Download all |
|---|---|---|
|
md5:c2530f6da9b22fcd3ef0d02975639a85
|
528.1 kB | Preview Download |
|
md5:aa4e7eedd64e06fab0f52e8c92526c84
|
1.2 MB | Preview Download |
Additional details
- PMCID
- PMC2941390
- Eprint ID
- 20172
- Resolver ID
- CaltechAUTHORS:20100928-091358513
- NS34407
- NIH
- 5-T32-GM07616
- NIH Predoctoral Fellowship
- Created
-
2010-09-28Created from EPrint's datestamp field
- Updated
-
2021-11-08Created from EPrint's last_modified field