Two-Bromoaryl-para-Quinone Methide: A Versatile Synthon for Carbocycles and Heterocycles
Related Experiment Video
Updated: Nov 7, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Priyanka Saikia1,2, Sumanta Sarkar1, Pranjal Gogoi1,2
1Chemical Science and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat, India.
Abstract:
para-Quinone Methides (p-QMs) are versatile reactive intermediates widely used in organic synthesis, particularly undergoing 1,6-Michael addition leading to the formation of complex organic frameworks. Over the years, numerous reactive partners associated with p-QMs, such as 2-hydroxyphenyl-, o-tosylaminophenyl-, and 1,5-enyne-substituted p-QMs, have been developed to access the core structures of a broad range of natural products and bioactive molecules. In contrast, p-QMs associated with haloarenes, particularly the 2-bromoaryl-substituted para-quinone methides, have also emerged as valuable synthons in organic synthesis; however, their reactivity and synthetic applications have not been comprehensively summarized. Therefore, this review systematically summarizes recent advances in the synthetic utilities of 2-bromoaryl-substituted para-quinone methides, with an emphasis on their reactivity under various reaction conditions, mechanistic insights, and substrate scope. Additionally, it summarizes the key transformations enabled by transition-metal catalysis and highlights their scope for C─C and C-heteroatom bond construction. Moreover, the future prospects and limitations of 2-bromoaryl-substituted para-quinone methide are also outlined.
Related Concept Videos
Five-Membered Heterocyclic Aromatic Compounds: Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)