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

研究成果: Article › 査読

1 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	317-320
ページ数	4
ジャーナル	Tetrahedron Letters
巻	58
号	4
DOI	https://doi.org/10.1016/j.tetlet.2016.12.009
出版ステータス	Published - 2017 1月 25

ASJC Scopus subject areas

生化学
創薬
有機化学

文献へのアクセス

10.1016/j.tetlet.2016.12.009

他のファイルとリンク

引用スタイル

@article{d1d9d536c3004fb6bae278046fbe7b15,

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

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.",

keywords = "Anilides, Benzylation, Ethers, Imidates, tert-Butyl",

author = "Tomoyuki Yamada and Shiori Tsukagoshi and Osamu Kitagawa",

year = "2017",

month = jan,

day = "25",

doi = "10.1016/j.tetlet.2016.12.009",

language = "English",

volume = "58",

pages = "317--320",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "4",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=85007493436&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85007493436&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2016.12.009

DO - 10.1016/j.tetlet.2016.12.009

M3 - Article

AN - SCOPUS:85007493436

SN - 0040-4039

VL - 58

SP - 317

EP - 320

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

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

抄録

ASJC Scopus subject areas

文献へのアクセス

他のファイルとリンク

フィンガープリント

引用スタイル