Yb(iii)-catalysed syn-thioallylation of ynamides

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Ynamides are versatile synthetic intermediates.
• Accessing highly substituted olefins remains a challenge in organic synthesis.

Purpose of the Study:

• To develop a novel catalytic method for the synthesis of thioamino-skipped-dienes.
• To explore the utility of ytterbium(III) catalysis in ynamide functionalization.

Main Methods:

• Syn-thioallylation of α-sulfide substituted ynamides.
• Utilizing ytterbium(III) as a catalyst.
• Reaction optimization and substrate scope evaluation.

Main Results:

• Successful synthesis of highly substituted thioamino-skipped-dienes.
• Broad substrate scope demonstrated, yielding tetrasubstituted olefins.
• Complete atom economy achieved in a single synthetic step.
• Extension to syn-selenoallylation for selenoamino dienes.

Conclusions:

• The developed ytterbium-catalyzed syn-thioallylation offers an efficient route to complex olefins.
• The methodology provides access to valuable thioamino-skipped-dienes and related compounds.
• Mechanistic insights were gained through DFT studies and control experiments.