Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines

Minyan Li; Baris Yucel; Jacqueline Jiménez; Madeline Rotella; Yue Fu; Patrick J. Walsh

doi:10.1002/adsc.201600075

Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines

Minyan Li, Baris Yucel, Jacqueline Jiménez, Madeline Rotella, Yue Fu, Patrick J. Walsh^*

^*Bu çalışma için yazışmadan sorumlu yazar

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Araştırma sonucu: ???type-name??? › Makale › bilirkişi

33 Atıf (Scopus)

Özet

An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box. (Figure presented.) .

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	1910-1915
Sayfa sayısı	6
Dergi	Advanced Synthesis and Catalysis
Hacim	358
Basın numarası	12
DOI'lar	https://doi.org/10.1002/adsc.201600075
Yayın durumu	Yayınlandı - 16 Haz 2016

Bibliyografik not

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Finansman

P.J.W. acknowledges the NIH (National Institute of General Medical Sciences NIGMS 104349). B.Y thanks the Scientific and Technical Research Council of Turkey for a TUBITAK-2219 fellowship. J. J. thanks CONACyT (México) for fellowships.

Finansörler	Finansör numarası
National Institutes of Health
National Institute of General Medical Sciences	104349
Consejo Nacional de Ciencia y Tecnología
Türkiye Bilimsel ve Teknolojik Araştirma Kurumu

Belgeye Erişim

10.1002/adsc.201600075

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

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title = "Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines",

abstract = "An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box. (Figure presented.) .",

keywords = "2-azaallyl anion, diarylmethylamines, NIXANTPHOS, regioselectivity, umpolung",

author = "Minyan Li and Baris Yucel and Jacqueline Jim{\'e}nez and Madeline Rotella and Yue Fu and Walsh, {Patrick J.}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = jun,

day = "16",

doi = "10.1002/adsc.201600075",

language = "English",

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pages = "1910--1915",

journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines

AU - Li, Minyan

AU - Yucel, Baris

AU - Jiménez, Jacqueline

AU - Rotella, Madeline

AU - Fu, Yue

AU - Walsh, Patrick J.

PY - 2016/6/16

Y1 - 2016/6/16

N2 - An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box. (Figure presented.) .

AB - An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a palladium-catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glove box. (Figure presented.) .

KW - 2-azaallyl anion

KW - diarylmethylamines

KW - NIXANTPHOS

KW - regioselectivity

KW - umpolung

UR - http://www.scopus.com/inward/record.url?scp=84969753034&partnerID=8YFLogxK

U2 - 10.1002/adsc.201600075

DO - 10.1002/adsc.201600075

M3 - Article

AN - SCOPUS:84969753034

SN - 1615-4150

VL - 358

SP - 1910

EP - 1915

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 12

ER -

Umpolung Synthesis of Diarylmethylamines via Palladium- Catalyzed Arylation of N-Benzyl Aldimines

Özet

Bibliyografik not

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

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