Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride

Jia Hao Pang; Bin Wang; Kohei Watanabe; Ryo Takita; Shunsuke Chiba

doi:10.1002/hlca.202100120

Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride

Jia Hao Pang, Bin Wang, Kohei Watanabe, Ryo Takita^*, Shunsuke Chiba^*

^*Corresponding author for this work

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

2 Citations (Scopus)

Abstract

A method for the synthesis of 1,3-diarylpropylamines through hydroalkylation of styrenes with benzylamines by potassium hydride has been developed. The protocol is initiated by solvothermal treatment of benzylamines with KH at 100 °C to generate deprotonated anionic species, which undergo selective C-alkylation with arylalkenes at 0 °C to ambient temperature to afford 1,3-diarylpropylamines as the major product.

Original language	English
Article number	e2100120
Journal	Helvetica Chimica Acta
Volume	104
Issue number	10
DOIs	https://doi.org/10.1002/hlca.202100120
Publication status	Published - Oct 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 Wiley-VHCA AG, Zurich, Switzerland

ASJC Scopus Subject Areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Keywords

alkylation
arylalkenes
benzylamines
carbanions
hydroalkylation
potassium hydride

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10.1002/hlca.202100120

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title = "Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride",

abstract = "A method for the synthesis of 1,3-diarylpropylamines through hydroalkylation of styrenes with benzylamines by potassium hydride has been developed. The protocol is initiated by solvothermal treatment of benzylamines with KH at 100 °C to generate deprotonated anionic species, which undergo selective C-alkylation with arylalkenes at 0 °C to ambient temperature to afford 1,3-diarylpropylamines as the major product.",

keywords = "alkylation, arylalkenes, benzylamines, carbanions, hydroalkylation, potassium hydride",

author = "Pang, \{Jia Hao\} and Bin Wang and Kohei Watanabe and Ryo Takita and Shunsuke Chiba",

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month = oct,

doi = "10.1002/hlca.202100120",

language = "English",

volume = "104",

journal = "Helvetica Chimica Acta",

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T1 - Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride

AU - Pang, Jia Hao

AU - Wang, Bin

AU - Watanabe, Kohei

AU - Takita, Ryo

AU - Chiba, Shunsuke

PY - 2021/10

Y1 - 2021/10

N2 - A method for the synthesis of 1,3-diarylpropylamines through hydroalkylation of styrenes with benzylamines by potassium hydride has been developed. The protocol is initiated by solvothermal treatment of benzylamines with KH at 100 °C to generate deprotonated anionic species, which undergo selective C-alkylation with arylalkenes at 0 °C to ambient temperature to afford 1,3-diarylpropylamines as the major product.

AB - A method for the synthesis of 1,3-diarylpropylamines through hydroalkylation of styrenes with benzylamines by potassium hydride has been developed. The protocol is initiated by solvothermal treatment of benzylamines with KH at 100 °C to generate deprotonated anionic species, which undergo selective C-alkylation with arylalkenes at 0 °C to ambient temperature to afford 1,3-diarylpropylamines as the major product.

KW - alkylation

KW - arylalkenes

KW - benzylamines

KW - carbanions

KW - hydroalkylation

KW - potassium hydride

UR - http://www.scopus.com/inward/record.url?scp=85115297946&partnerID=8YFLogxK

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U2 - 10.1002/hlca.202100120

DO - 10.1002/hlca.202100120

M3 - Article

AN - SCOPUS:85115297946

SN - 0018-019X

VL - 104

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 10

M1 - e2100120

ER -

Hydroalkylation of Styrenes with Benzylamines by Potassium Hydride

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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