TY - JOUR
T1 - DDQ as a versatile and easily recyclable oxidant
T2 - a systematic review
AU - Alsharif, Meshari A.
AU - Raja, Qandeel Alam
AU - Majeed, Nida Abdul
AU - Jassas, Rabab S.
AU - Alsimaree, Abdulrahman A.
AU - Sadiq, Amina
AU - Naeem, Nafeesa
AU - Mughal, Ehsan Ullah
AU - Alsantali, Reem I.
AU - Moussa, Ziad
AU - Ahmed, Saleh A.
N1 - Funding Information:
The authors are thankful to the Deanship of Scientific Research at Umm Al-Qura University for financial support under grant code 19-SCI-1-01-0008. The authors are also highly grateful to the Higher Education Commission of Pakistan (HEC) for providing financial assistance under Project No. (NRPU-6484).
Funding Information:
The authors are thankful to the Deanship of Scientic Research at Umm Al-Qura University for nancial support under grant code 19-SCI-1-01-0008. The authors are also highly grateful to the Higher Education Commission of Pakistan (HEC) for providing nancial assistance under Project No. (NRPU-6484).
Publisher Copyright:
© The Royal Society of Chemistry 2021.
PY - 2021/8/18
Y1 - 2021/8/18
N2 - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is the most widely used quinone with a high reduction potential, and it commonly mediates hydride transfer reactions and shows three accessible oxidation states: quinone (oxidized), semiquinone (one-electron-reduced), and hydroquinone (two-electron-reduced). DDQ has found broad utility as a stoichiometric oxidant in the functionalization of activated C-H bonds and the dehydrogenation of saturated C-C, C-O, and C-N bonds. The cost and toxicity of DDQ triggered recent efforts to develop methods that employ catalytic quantities of DDQ in combination with alternative stoichiometric oxidants. The aerobic catalytic approach was established for the selective oxidation of non-sterically hindered electron-rich benzyl methyl ethers and benzylic alcohols, and effectively extended to the oxidative deprotection ofp-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.
AB - 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is the most widely used quinone with a high reduction potential, and it commonly mediates hydride transfer reactions and shows three accessible oxidation states: quinone (oxidized), semiquinone (one-electron-reduced), and hydroquinone (two-electron-reduced). DDQ has found broad utility as a stoichiometric oxidant in the functionalization of activated C-H bonds and the dehydrogenation of saturated C-C, C-O, and C-N bonds. The cost and toxicity of DDQ triggered recent efforts to develop methods that employ catalytic quantities of DDQ in combination with alternative stoichiometric oxidants. The aerobic catalytic approach was established for the selective oxidation of non-sterically hindered electron-rich benzyl methyl ethers and benzylic alcohols, and effectively extended to the oxidative deprotection ofp-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.
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U2 - 10.1039/d1ra04575j
DO - 10.1039/d1ra04575j
M3 - Review article
AN - SCOPUS:85116491095
SN - 2046-2069
VL - 11
SP - 29826
EP - 29858
JO - RSC Advances
JF - RSC Advances
IS - 47
ER -