Related Experiment Video
Updated: Apr 18, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Regioselective derivatizations of a tribrominated atropisomeric benzamide scaffold
Kimberly T Barrett1, Scott J Miller
1Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520-8107, United States.
Abstract:
The enantioselective synthesis of atropisomeric, tribrominated benzamides and subsequent regioselective transformations to afford derivatized, axially chiral molecules is reported. The enantioenriched tribromides were carried through sequential Pd-catalyzed cross-coupling and lithium-halogen exchange with high regioselectivity and enantioretention. A variety of complexity-generation functional group installations were performed to create a library of homochiral benzamides. The potential utility of these molecules is demonstrated by using a phosphino benzamide derivative as an asymmetric ligand in a Pd-catalyzed allylic alkylation.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
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...
Reactions at the Benzylic Position: Halogenation
NMR Spectroscopy of Benzene Derivatives
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...

