Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent

Tomoyuki Yamada; Shiori Tsukagoshi; Osamu Kitagawa

doi:10.1016/j.tetlet.2016.12.009

Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent

Tomoyuki Yamada, Shiori Tsukagoshi, Osamu Kitagawa

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The reaction of methyl iodide with an anilide anion prepared from 2,4,6-tri-tert-butylanilide and NaH in CH₃CN gave N-methyl anilide (N-alkylation product) as a major product, while in the reaction of benzyl bromide with the anilide anion in DMF, O-benzyl imidate (O-alkylation product) was obtained with almost complete selectivity. The treatment of O-benzyl imidate with alcohols and carboxylic acids in the presence of trifluoromethane sulfonic acid gave benzyl ethers and benzyl esters, respectively.

Original language	English
Pages (from-to)	317-320
Number of pages	4
Journal	Tetrahedron Letters
Volume	58
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2016.12.009
Publication status	Published - 2017 Jan 25

Keywords

Anilides
Benzylation
Ethers
Imidates
tert-Butyl

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2016.12.009

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abstract = "The reaction of methyl iodide with an anilide anion prepared from 2,4,6-tri-tert-butylanilide and NaH in CH3CN gave N-methyl anilide (N-alkylation product) as a major product, while in the reaction of benzyl bromide with the anilide anion in DMF, O-benzyl imidate (O-alkylation product) was obtained with almost complete selectivity. The treatment of O-benzyl imidate with alcohols and carboxylic acids in the presence of trifluoromethane sulfonic acid gave benzyl ethers and benzyl esters, respectively.",

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T1 - Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent

AU - Yamada, Tomoyuki

AU - Tsukagoshi, Shiori

AU - Kitagawa, Osamu

PY - 2017/1/25

Y1 - 2017/1/25

N2 - The reaction of methyl iodide with an anilide anion prepared from 2,4,6-tri-tert-butylanilide and NaH in CH3CN gave N-methyl anilide (N-alkylation product) as a major product, while in the reaction of benzyl bromide with the anilide anion in DMF, O-benzyl imidate (O-alkylation product) was obtained with almost complete selectivity. The treatment of O-benzyl imidate with alcohols and carboxylic acids in the presence of trifluoromethane sulfonic acid gave benzyl ethers and benzyl esters, respectively.

AB - The reaction of methyl iodide with an anilide anion prepared from 2,4,6-tri-tert-butylanilide and NaH in CH3CN gave N-methyl anilide (N-alkylation product) as a major product, while in the reaction of benzyl bromide with the anilide anion in DMF, O-benzyl imidate (O-alkylation product) was obtained with almost complete selectivity. The treatment of O-benzyl imidate with alcohols and carboxylic acids in the presence of trifluoromethane sulfonic acid gave benzyl ethers and benzyl esters, respectively.

KW - Anilides

KW - Benzylation

KW - Ethers

KW - Imidates

KW - tert-Butyl

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DO - 10.1016/j.tetlet.2016.12.009

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JO - Tetrahedron Letters

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Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent

Abstract

Keywords

ASJC Scopus subject areas

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