Dual Role of N‐Bromosuccinimide as Oxidant and Succinimide Surrogate in Domino One‐Pot Oxidative Amination of Benzyl Alcohols for the Synthesis of α–Imido Ketones | Zendy

Muneeswara Madithedu | Zendy; Muthukumar Alagesan | Zendy; Sekar Govindasamy | Zendy

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Dual Role of N‐Bromosuccinimide as Oxidant and Succinimide Surrogate in Domino One‐Pot Oxidative Amination of Benzyl Alcohols for the Synthesis of α–Imido Ketones

Author(s) -

Muneeswara Madithedu,

Muthukumar Alagesan,

Sekar Govindasamy

Publication year - 2018

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201803465

Subject(s) - succinimide , chemistry , amination , ketone , benzyl alcohol , halogenation , organic chemistry , n bromosuccinimide , medicinal chemistry , catalysis

A transition‐metal‐free oxidative amination of secondary benzyl alcohols has been developed using N ‐bromosuccinimide as the oxidant and source of succinimide. The control experiments revealed that the transformation underwent via oxidation of alcohol to ketone, α‐bromination of ketone and diazabicyclo[5.4.1]undec‐7‐ene (DBU) base‐mediated nucleophilic substitution of the by‐product succinimide. Various substituted benzyl alcohols and N ‐bromoimides were examined to form α‐imido ketones in short reaction timespans. The protocol was successfully extended to a gram scale reaction.

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