title: Synthesis ofN,N-Diethylbenzamides via a Non-Classical Mitsunobu Reaction.
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 non-classical mechanism involving the existence of an acyloxyphosphonium ion.
authors.affiliation: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
authors.forename: J Mason
authors.initials: JM
authors.lastname: Hoffman
authors.affiliation: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
authors.forename: Justin N
authors.initials: JN
authors.lastname: Miller
authors.affiliation: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
authors.forename: Margaret E
authors.initials: ME
authors.lastname: Gardner
authors.affiliation: Department of Chemistry and Biochemistry, Colorado College, 14 East Cache La Poudre, Colorado Springs, CO, 80903-3298, USA.
authors.forename: Danielle R
authors.initials: DR
authors.lastname: LePar
authors.affiliation: Department of Chemistry, Sewanee: The University of the South, 735 University Avenue, Sewanee, TN 37383-1000, USA.
authors.forename: Rongson
authors.initials: R
authors.lastname: Pongdee
keywords: Mitsunobu reaction; acylation; amides