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- Title
Enantioselective Arylation of Sulfenamides to Access Sulfilimines Enabled by Palladium Catalysis.
- Authors
Yuan, Yin; Han, Yidan; Zhang, Zhi‐kun; Sun, Shijin; Wu, Ke; Yang, Junfeng; Zhang, Junliang
- Abstract
Sulfur‐containing functional groups have garnered considerable attention due to their common occurrence in ligands, pharmaceuticals, and insecticides. Nevertheless, enantioselective synthesis of sulfilimines, particularly diaryl sulfilimines remains a challenging and persistent goal. Herein we report a highly enantio‐ and chemoselective cross–coupling of sulfenamides with aryl diazonium salt to construct diverse S(IV) stereocenters by Pd catalysis. Bisphosphine ligands bearing sulfinamide groups play a crucial role in achieving high reactivity and selectivity. This approach provides a general, modular and divergent framework for quickly synthesizing chiral sulfilimines and sulfoximines that are otherwise challenging to access. In addition, the origins of the high chemoselectivity and enantioselectivity were extensively investigated using density functional theory calculations.
- Subjects
ASYMMETRIC synthesis; DENSITY functional theory; DIAZONIUM compounds; FUNCTIONAL groups; ARYLATION
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 37, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202409541