Litcius/Paper detail

DDQ as a versatile and easily recyclable oxidant: a systematic review

Meshari A. Alsharif, Qandeel Alam Raja, Nida Abdul Majeed, Rabab S. Jassas, Abdulrahman A. Alsimaree, Amina Sadiq, Nafeesa Naeem, Ehsan Ullah Mughal, Reem I. Alsantali, Ziad Moussa, Saleh A. Ahmed

2021RSC Advances104 citationsDOIOpen Access PDF

Abstract

-methoxybenzyl ethers to generate the alcohols in high selectivity. A combination of DDQ and protic acid is known to oxidize several aromatic donors to the corresponding cation radicals. The excited-state DDQ converts benzyls, heteroarenes, fluoroarenes, benzene, and olefins into their radical cation forms as well as chloride and other anions into their respective radicals. These reactive intermediates have been employed for the generation of C-C and C-X (N, O, or Cl) bonds in the synthesis of valuable natural products and organic compounds. To the best of our knowledge, however, there is still no review article exclusively describing the applications of DDQ in organic synthesis. Therefore, in the present review, we provide an overview of DDQ-induced organic transformations with their scope, limitations and the proposed reaction mechanisms.

Topics & Concepts

HydroquinoneQuinoneSemiquinoneChemistryHydrideElectron transferRedoxPhotochemistryCombinatorial chemistryOrganic chemistryHydrogenAxial and Atropisomeric Chirality SynthesisSynthesis of Indole DerivativesOxidative Organic Chemistry Reactions