Work

Synthesis of N,N-Diethylbenzamides via a Nonclassical Mitsunobu Reaction

Year: 2013

Type: article

Abstract: The use of the Mitsunobu reaction for the synthesis of N,N-diethylbenzamides affords ortho-, meta-, and para-substituted benzamides containing both electron-donating and electron-withdrawing groups. While the preparation of numerous functional groups has been efficiently demonstrated employing the Mitsunobu reaction, our methodology represents the first application of the Mitsunobu reaction for the construction of benzamides using benzoic acid and amine starting materials. Moreover, this synthetic transformation is believed to proceed via a nonclassical mechanism involving the existence of an acyloxyphosphonium ion. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

Source: Synthetic Communications

DOI: 10.1080/00397911.2013.839796

Authors: J. Mason Hoffman, Justin N. Miller, Margaret E. Gardner, Danielle R. LePar, Rongson Pongdee

Institutions: Sewanee: The University of the South, Colorado College

Language: English

Topic: Phosphorus compounds and reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, University of Notre Dame, American Chemical Society Petroleum Research Fund, National Institute of Allergy and Infectious Diseases

Award: Glycodiversification of Angucycline Antibiotics