Related Experiment Video
Updated: Jun 18, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Access to Valuable Chalcogen-Containing Biaryl Derivatives via Regioselective 2,2'-Dichalcogenation of 2-Bromobiaryls
Yike Bai1, Feng Ouyang1, Rong Chen1
1College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, Hunan, People's Republic of China.
Abstract:
The regioselective installation of chalcogen atoms into biaryl scaffolds is an important synthetic task due to the great value of chalcogen-containing biaryl derivatives in many fields. Here we undertake this task by developing a regioselective 2,2'-dichalcogenation of 2-bromobiaryls with common chalcogen sources using an organolanthanum-mediated one-pot, two-step protocol. This strategy features high regioselectivity, readily available substrates, transition-metal-free conditions, and performance superior to those of previous methods, thereby demonstrating the unique advantages of organolanthanum reagents in organic synthesis.
More Related Videos
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Regioselectivity of Electrophilic Additions-Peroxide Effect
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene