N-Hydroxyhomoazaadamantanone and its complexes with dioxo-molybdenum(VI) and copper(II): synthesis and structure

Compared to the a-functionalization of aldehydes, ketones,even esters,the direct a-modification of amides is still achallenge because of the low acidity of a-CH groups.The afunctionalization of N À H( primary and secondary) amides, containing both an unactived a-C À Hbond and acompetitively active N À Hbond, remains elusive.Shownherein is the general and efficient oxidative a-oxyamination and hydroxylation of aliphatic amides including secondary NÀHa mides.T his transition-metal-free chemistry with high chemoselectivity provides an efficient approach to a-hydroxy amides.T his oxidative protocol significantly enables the selective functionalization of inert a-C À Hbonds with the complete preservation of active N À Hb ond.Aldehydes,ketones,esters,acids,and amides are very Scheme 1. The significance and challenges for the a-modification of aliphatic amides. Tf = trifluoromethanesulfonyl, Ts = 4-toluenesulfonyl.

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Selective α‐Oxyamination and Hydroxylation of Aliphatic Amides

Lin

Huang

et al. 2017

Angewandte Chemie

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show abstract

Selective α‐Oxyamination and Hydroxylation of Aliphatic Amides

Lin

Huang

et al. 2017

Angew Chem Int Ed

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Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N-H (primary and secondary) amides, containing both an unactived α-C-H bond and a competitively active N-H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N-H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C-H bonds with the complete preservation of active N-H bond.

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Lipophilic chloro-oxo-bis(hydroxamato)vanadium(V) complexes: synthesis methods and structure

et al. 2020

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N-Hydroxyhomoazaadamantanone and its complexes with dioxo-molybdenum(VI) and copper(II): synthesis and structure

Cited by 9 publications

References 19 publications

Selective α‐Oxyamination and Hydroxylation of Aliphatic Amides

Selective α‐Oxyamination and Hydroxylation of Aliphatic Amides

Selective α‐Oxyamination and Hydroxylation of Aliphatic Amides

Lipophilic chloro-oxo-bis(hydroxamato)vanadium(V) complexes: synthesis methods and structure

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