Borane catalysed annulative sulfenylation of internal alkynes: towards the synthesis and study of fused heterocycles
Abstract
]benzofurans. These products exhibit fluorescence from locally excited states, consistent with their large singlet-triplet energy gaps. Additionally, the cyclisation of aryl propargyl ethers, 4-diphenylbut-1-yne and a tosyl-protected propargylaniline afforded sulfenylated 6-membered products (7 examples, up to 94% yield). Density functional theory (DFT) calculations, corroborated by initial kinetics, helped to understand the order and rate of the reaction and support a mechanism in which thiirenium ions are involved as key intermediates in the formation of the observed products.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Catalytic C–H Functionalization Methods
Radical Photochemical Reactions
Publication details
- Journal / source
- Chemical Science
- Publisher
- Royal Society of Chemistry (RSC)
- Volume
- 17
- Issue
- 23
- Pages
- 11682–11692
- Publication date
- 1 January 2026
- Language
- EN