Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane

Yuki Kayashima; Masaaki Komatsuda; Kei Muto; Junichiro Yamaguchi

doi:10.1246/cl.200216

Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane

Yuki Kayashima, Masaaki Komatsuda, Kei Muto, Junichiro Yamaguchi^*

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

A dearomative C4-allylation of benzyl ammoniums with allyltributylstannane by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic CN bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- A nd C3-selective functionalizations of benzyl amine derivatives, the present reaction can provide a new synthetic option for the synthesis of multi-substituted alicyclic compounds as well as aromatic compounds.

Original language	English
Pages (from-to)	836-839
Number of pages	4
Journal	Chemistry Letters
Volume	49
Issue number	7
DOIs	https://doi.org/10.1246/cl.200216
Publication status	Published - 2020 Jul

Keywords

Benzyl ammoniums
Dearomatization
Palladium catalyst

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.200216

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title = "Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane",

abstract = "A dearomative C4-allylation of benzyl ammoniums with allyltributylstannane by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic CN bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- A nd C3-selective functionalizations of benzyl amine derivatives, the present reaction can provide a new synthetic option for the synthesis of multi-substituted alicyclic compounds as well as aromatic compounds.",

keywords = "Benzyl ammoniums, Dearomatization, Palladium catalyst",

author = "Yuki Kayashima and Masaaki Komatsuda and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP19H02726 (to J.Y.), JP18H04661 (Hybrid Catalysis), JP19K15573, and The SATOMI Scholarship Foundation (to K.M.). The Materials Characterization Central Laboratory at Waseda University is acknowledged for the support of HRMS measurement. Publisher Copyright: {\textcopyright} 2020 Chemical Society of Japan. All rights reserved.",

year = "2020",

month = jul,

doi = "10.1246/cl.200216",

language = "English",

volume = "49",

pages = "836--839",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "7",

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T1 - Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane

AU - Kayashima, Yuki

AU - Komatsuda, Masaaki

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP19H02726 (to J.Y.), JP18H04661 (Hybrid Catalysis), JP19K15573, and The SATOMI Scholarship Foundation (to K.M.). The Materials Characterization Central Laboratory at Waseda University is acknowledged for the support of HRMS measurement. Publisher Copyright: © 2020 Chemical Society of Japan. All rights reserved.

PY - 2020/7

Y1 - 2020/7

N2 - A dearomative C4-allylation of benzyl ammoniums with allyltributylstannane by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic CN bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- A nd C3-selective functionalizations of benzyl amine derivatives, the present reaction can provide a new synthetic option for the synthesis of multi-substituted alicyclic compounds as well as aromatic compounds.

AB - A dearomative C4-allylation of benzyl ammoniums with allyltributylstannane by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic CN bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- A nd C3-selective functionalizations of benzyl amine derivatives, the present reaction can provide a new synthetic option for the synthesis of multi-substituted alicyclic compounds as well as aromatic compounds.

KW - Benzyl ammoniums

KW - Dearomatization

KW - Palladium catalyst

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DO - 10.1246/cl.200216

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SN - 0366-7022

VL - 49

SP - 836

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JO - Chemistry Letters

JF - Chemistry Letters

IS - 7

ER -

Pd-catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane

Abstract

Keywords

ASJC Scopus subject areas

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