Related Experiment Video
Updated: Dec 20, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Cobalt-Catalyzed Switchable Intramolecular Thioenolization/C-H Thiolation and C(sp2)-H/C(sp3)-H Dehydrogenative
Zhi Yao1, Zhongliang Cai1, Long Zhen1
1School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Road, Shanghai 200241, China.
Abstract:
Mild cobalt-catalyzed switchable regioselective and chemoselective thioenolization/C-H thiolation and C(sp2)-H/C(sp3)-H dehydrogenative couplings of N-aryl-N-alkyl-thioamides are developed, providing 2-methylene-2,3-dihydrobenzo[d]thiazoles and thio-oxindoles in moderate to excellent yields from the same precursors, respectively. Details mechanistic studies suggest that the thioenolization/C-H thiolation process involves a radical mechanism, whereas the C(sp2)-H/C(sp3)-H dehydrogenative coupling might proceed through an electrophilic cobaltation(III) pathway. Thus, the selectivity for either product is achieved by accessing unique catalytic cycles involving different valence states for cobalt.
Related Concept Videos
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Preparation and Reactions of Thiols
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

