Related Experiment Video
Updated: May 30, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Iron-Catalyzed Dearomatizing Reductive Cyclization of Arenes
Ling-Jie Song1, Xiao-Dong Zhang1, Zheng-Hao Jin1
1College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China.
Abstract:
An efficient iron-catalyzed intramolecular dearomatizing reductive cyclization of arenes has been developed. By employing FeBr2 as the catalyst, tripyridine as the ligand, and Mn powder as the reductant, a series of spiro-cyclohexadienes and dihydronaphthalenes were afforded in moderate to excellent yields with aryliodine-tethered benzyl tert-butyl carbonate or naphthalene derivatives as substrates. In addition, several synthetic transformations were conducted to demonstrate the utility of the reaction, and control experiments were carried out to gain insight into the mechanism.
Related Concept Videos
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.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Preparation of Amines: Reductive Amination of Aldehydes and Ketones

