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Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base.

ABSTRACT: Metal-free reaction conditions featuring oxygen and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were employed for the selective oxidation of benzyl amines and active methylene compounds to afford various amides and ketones. Owing to the strong basicity of guanidine bases, TBD is presumed to play an important role in the cleavage of the C-H bond at the benzylic position of peroxide intermediates, which were formed by the reaction with oxygen.

SUBMITTER: Lee S

PROVIDER: S-EPMC6822219 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Aerobic Oxidation of Benzylic Carbons Using a Guanidine Base.

Lee Seulchan S Kim Si Ae SA Jang Hye-Young HY

ACS omega 20191015 18

Metal-free reaction conditions featuring oxygen and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were employed for the selective oxidation of benzyl amines and active methylene compounds to afford various amides and ketones. Owing to the strong basicity of guanidine bases, TBD is presumed to play an important role in the cleavage of the C-H bond at the benzylic position of peroxide intermediates, which were formed by the reaction with oxygen. ...[more]

PMID: 31681903

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