Pd-Catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allylstannanes

Yuki Kayashima; Masaaki Komatsuda; Kei Muto; Junichiro Yamaguchi

doi:10.26434/chemrxiv.12015663.v1

Pd-Catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allylstannanes

Yuki Kayashima, Masaaki Komatsuda, Kei Muto, Junichiro Yamaguchi

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

Abstract

A dearomative C4-allylation of benzyl ammoniums with allylstannanes by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic C–N bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- and 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
Journal	Unknown Journal
DOIs	https://doi.org/10.26434/chemrxiv.12015663.v1
Publication status	Published - 2020 Mar 21

Keywords

Benzyl Ammoniums
Dearomatization
Palladium Catalyst

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)
Materials Science(all)

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title = "Pd-Catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allylstannanes",

abstract = "A dearomative C4-allylation of benzyl ammoniums with allylstannanes by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic C–N bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- and 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",

year = "2020",

month = mar,

day = "21",

doi = "10.26434/chemrxiv.12015663.v1",

language = "English",

journal = "Nuclear Physics A",

issn = "0375-9474",

publisher = "Elsevier",

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TY - JOUR

T1 - Pd-Catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allylstannanes

AU - Kayashima, Yuki

AU - Komatsuda, Masaaki

AU - Muto, Kei

AU - Yamaguchi, Junichiro

PY - 2020/3/21

Y1 - 2020/3/21

N2 - A dearomative C4-allylation of benzyl ammoniums with allylstannanes by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic C–N bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- and 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 allylstannanes by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic C–N bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- and 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 - 10.26434/chemrxiv.12015663.v1

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JF - Nuclear Physics A

SN - 0375-9474

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