Optimizing Amine‐Mediated Alkyne–Allene Isomerization to Improve Benzannulation Cascades: Synergy between Theory and Experiments

• Published in: European journal of organic chemistry Vol. 2019; no. 2-3; pp. 512 - 518
• Main Authors: dos Passos Gomes, Gabriel, Morrison, Alec E., Dudley, Gregory B., Alabugin, Igor V.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 23.01.2019
• Subjects: Alkynes; Allene; Allenes; Benzannulation; Cascades; Computation; Design of experiments; Guanidines; Impact analysis; Isomerization; Proton transfer; Protons; Substrates

A synergy between theory and experiments leads to a milder protocol for base‐mediated high‐temperature benzannulation of alkynylpyridine substrates. Computational analysis identifies mechanistic and energetic nuances in the previously postulated 1,3‐proton transfer isomerization which results in rep...