Synthesis of Axially Chiral Allenes by Pd-Catalyzed Thianthrene-Mediated Functionalization of Alkynes with Arenes
Abstract
A strategy based on sequential "C-H thianthrenation/Pd-catalyzed asymmetric Heck reaction" was designed to synthesize trisubstituted chiral allenes from nonprefunctionalized arenes directly. This innovative approach successfully addressed challenging cyclic and acyclic systems while enabling the late-stage modification of complex small molecules. The methodology exhibited remarkable robustness through its successful implementation in a gram-scale reaction and the recycling of thianthrene. Density functional theory computation results reveal that the enantioselective step follows a base-accelerated β-H elimination mechanism.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Axial and Atropisomeric Chirality Synthesis
Sulfur-Based Synthesis Techniques
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 4
- Pages
- 1300–1305
- Publication date
- 15 January 2026
- Language
- EN