Diboron reagents in the deoxygenation of nitrones
Emily L Vargas1, Mario Franco1, Inés Alonso1,2
1Department of Organic Chemistry, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. belen.cid@uam.es.
Abstract:
B2nep2 efficiently promotes the N-O cleavage of nitrones to form imines in very high yields via a simple, efficient, sustainable, functional group tolerant and scalable protocol. The reaction occurs in the absence of additives through a concerted mechanism. We demonstrated that DMPO and TEMPO, typically used as radical traps, are also deoxygenated by diboron reagents, which demonstrates their limitation as mechanistic probes.
Related Concept Videos
Nitrosation of Enols
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Hydroboration-Oxidation of Alkenes
Preparation of Nitriles
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.


