Related Experiment Video
Updated: Jan 21, 2026

Upper-extremity Approach for Secondary Access in Transfemoral Transcatheter Aortic Valve Implantation
Published on: August 8, 2025
trans-Hydroboration of Propiolamides: Access to Primary and Secondary (E)-β-Borylacrylamides
R Justin Grams1, Russell G Fritzemeier1, Carla Slebodnick1
1Department of Chemistry, Virginia Tech, 900 West Campus Drive, Blacksburg, Virginia 24061, United States.
Abstract:
A base-mediated trans-hydroboration of propiolamides that provides access to previously elusive primary and secondary (E)-β-borylacrylamide products has been developed. In the presence of n-butyllithium and pinacolborane, complete regioselectivity and stereoselectivity is observed, affording the corresponding vinylboronate products in up to 91% yield. A wide variety of primary and secondary amides served as efficient substrates for this transformation. A plausible reaction mechanism that involves substrate-assisted activation and a key intramolecular cyclization is discussed.
Related Concept Videos
Primary and Secondary Growth in Roots and Shoots
Primary and Secondary Reinforcers
Effective reinforcers for humans vary depending on the individual and the context. Primary reinforcers, such as food, water, sleep, shelter, and pleasure, have inherent value and satisfy basic biological...
Hydroboration-Oxidation of Alkenes
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Secondary Active Transport
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.

