Reductive amination of acetals by anilines in the presence of triethylsilane and iodine

Xue Lin Zhang; Pan Yu; Yong Wei Wu; Qin Pei Wu; Qing Shan Zhang

doi:10.3184/174751914X13946178288518

Reductive amination of acetals by anilines in the presence of triethylsilane and iodine

Xue Lin Zhang
, Pan Yu
, Yong Wei Wu
, Qin Pei Wu^*
, Qing Shan Zhang

^*Corresponding author for this work

Beijing Institute of Technology

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

7 Citations (Scopus)

Abstract

A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I₂ and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.

Original language	English
Pages (from-to)	261-264
Number of pages	4
Journal	Journal of Chemical Research
Volume	38
Issue number	5
DOIs	https://doi.org/10.3184/174751914X13946178288518
Publication status	Published - May 2014
Externally published	Yes

Keywords

Acetals
Alkylation of amines
Secondary amine
Triethylsilane

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10.3184/174751914X13946178288518

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title = "Reductive amination of acetals by anilines in the presence of triethylsilane and iodine",

abstract = "A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.",

keywords = "Acetals, Alkylation of amines, Secondary amine, Triethylsilane",

author = "Zhang, \{Xue Lin\} and Pan Yu and Wu, \{Yong Wei\} and Wu, \{Qin Pei\} and Zhang, \{Qing Shan\}",

year = "2014",

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doi = "10.3184/174751914X13946178288518",

language = "English",

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T1 - Reductive amination of acetals by anilines in the presence of triethylsilane and iodine

AU - Zhang, Xue Lin

AU - Yu, Pan

AU - Wu, Yong Wei

AU - Wu, Qin Pei

AU - Zhang, Qing Shan

PY - 2014/5

Y1 - 2014/5

N2 - A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.

AB - A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.

KW - Acetals

KW - Alkylation of amines

KW - Secondary amine

KW - Triethylsilane

UR - https://www.scopus.com/pages/publications/84901041507

U2 - 10.3184/174751914X13946178288518

DO - 10.3184/174751914X13946178288518

M3 - Article

AN - SCOPUS:84901041507

SN - 1747-5198

VL - 38

SP - 261

EP - 264

JO - Journal of Chemical Research

JF - Journal of Chemical Research

IS - 5

ER -

Reductive amination of acetals by anilines in the presence of triethylsilane and iodine

Abstract

Keywords

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