Mn(OAc)3—an efficient oxidant for regeneration of DDQ: deprotection of p-methoxy benzyl ethers

Sharma, G. V. M.; Lavanya, B.; Arulprakasajothi, M.; Krishna, Palakodety Radha

doi:10.1016/s0040-4039(00)01855-4

Cited by 60 publications

(32 citation statements)

References 10 publications

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“…The additional impediments in using DDQ are the high cost and high molecular weight of this oxidant. Therefore, there are sustained efforts to address these issues by attempting to employ DDQ in a catalytic amount and regenerate DDQ from the resulting DDQH 2 by using various co‐oxidants such as FeCl 3 ,6a Mn(OAc) 3 ,6b,c MnO 2 ,7, and so forth (Scheme ). However, most of these efforts resulted in using a large excess (3–6 equiv) of inorganic co‐oxidants, which is one of the major setbacks due to toxicity and environmental concerns.…”

Section: Methodsmentioning

confidence: 99%

CDC Reactions of N‐Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: CH Activation under Aerobic Conditions

Alagiri

Devadig

Prabhu

2012

Chemistry A European J

149

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An oxidative cross‐dehydrogenative coupling (CDC) reaction for the formation of CC and CP bonds is disclosed using a catalytic amount of DDQ (10 mol %) under aerobic conditions (see scheme). This unprecedented environmentally benign strategy of using AIBN (10 mol %) and molecular oxygen to regenerate DDQ exhibits a larger substrate scope. For the first time, an efficient utility of 4‐hydroxycoumarins as pronucleophiles for CDC is presented.

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Section: Methodsmentioning

confidence: 99%

CDC Reactions of N‐Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: CH Activation under Aerobic Conditions

Alagiri

Devadig

Prabhu

2012

Chemistry A European J

149

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“…was successfully applied to the deprotection of p-meth-A C H T U N G T R E N N U N G oxybenzyl ethers. [15] Very recently, Floreancig and coworker described that a number of oxidation reactions including oxidative cyclization, deprotection and aromatization, can be effected by using catalytic DDQ (0.15-0.2 equiv.) with a large excess of MnO 2 (up to 6 equiv.)…”

Section: Introductionmentioning

confidence: 99%

2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)/tert‐Butyl Nitrite/Oxygen: A Versatile Catalytic Oxidation System

et al. 2011

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A new catalytic oxidation system using catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite with molecular oxygen serving as the environmentally benign, terminal oxidant has been developed. This aerobic catalytic system was established for the selective oxidation of non-sterically hindered benzylic alcohols and electron-rich benzyl methyl ethers, and successfully extended to an application in the oxidative deprotection of PMB ethers to the alcohols in high selectivity.

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“…7 Mn(OAc) 3 , which functions as a mild single electron acceptor, 8 has also been used for regeneration of DDQ in the removal of PMB protecting groups. 9 While this previous work did not include the oxidation of alcohols, we wished to determine whether this or a similar protocol would be amenable to our needs.. As a result of investigating this question, we are now pleased to report a new, modified catalytic oxidation procedure that is simple to perform, provides short reaction times, utilizes a readily prepared co-oxidant, and is not only selective for allylic and benzylic alcohols but which also exhibits selectivity for allylic alcohols in the presence of benzylic alcohols.…”

mentioning

confidence: 99%

Selective Oxidation of Benzylic and Allylic Alcohols Using Mn(OAc)₃/Catalytic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

et al. 2011

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A practical, chemoselective oxidation of alcohols employing catalytic quantities of DDQ as the oxidant and Mn(OAc)3 as the co-oxidant is described. Electron–rich benzylic alcohols are oxidized efficiently to their corresponding carbonyls, but less electron–rich benzylic alcohols remain unchanged. Allylic alcohols are rapidly oxidized to their corresponding aldehyde or ketone counterparts in high yields. This protocol is operationally simple, employs an inexpensive source of Mn(OAc)3, has short reaction times, and exhibits a significant chemoselectivity favoring allylic alcohols over benzylic alcohols. This procedure also avoids the use of the very large excesses of reagents and sometimes poor reproducibility that characterize previously developed reagents such as MnO2.

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Mn(OAc)3—an efficient oxidant for regeneration of DDQ: deprotection of p-methoxy benzyl ethers

Cited by 60 publications

References 10 publications

CDC Reactions of N‐Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: CH Activation under Aerobic Conditions

CDC Reactions of N‐Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: CH Activation under Aerobic Conditions

2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)/tert‐Butyl Nitrite/Oxygen: A Versatile Catalytic Oxidation System

Selective Oxidation of Benzylic and Allylic Alcohols Using Mn(OAc)₃/Catalytic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

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Mn(OAc)3—an efficient oxidant for regeneration of DDQ: deprotection of p-methoxy benzyl ethers

Cited by 60 publications

References 10 publications

CDC Reactions of N‐Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: CH Activation under Aerobic Conditions

CDC Reactions of N‐Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: CH Activation under Aerobic Conditions

2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)/tert‐Butyl Nitrite/Oxygen: A Versatile Catalytic Oxidation System

Selective Oxidation of Benzylic and Allylic Alcohols Using Mn(OAc)3/Catalytic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

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Selective Oxidation of Benzylic and Allylic Alcohols Using Mn(OAc)₃/Catalytic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone