Direct Synthesis of β-Amino Aldehydes from Linear Allylic Esters Using O2as the Sole Oxidant

Shu Hui Lei; Ya Zhong; Xian Peng Cai; Qing Huang; Jian Ping Qu; Yan Biao Kang

doi:10.1021/acs.orglett.1c03619

Direct Synthesis of β-Amino Aldehydes from Linear Allylic Esters Using O₂as the Sole Oxidant

Shu Hui Lei, Ya Zhong, Xian Peng Cai, Qing Huang, Jian Ping Qu, Yan Biao Kang

School of Chemistry and Moleculai Engineering

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

3 Scopus citations

Abstract

A tandem isomerization-anti-Markovnikov oxidation of linear allylic imidic esters is developed using bis(benzonitrile)palladium chloride as the catalyst and O2 as the sole oxidant, regiospecifically giving β-amino aldehydes as the product. tert-Butyl nitrite works as a simple, and the only, redox cocatalyst. tBuOH proves to be a crucial solvent for achieving excellent yield and specificity toward anti-Markovnikov aldehyde products.

Original language	English
Pages (from-to)	9273-9276
Number of pages	4
Journal	Organic Letters
Volume	23
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.1c03619
State	Published - 3 Dec 2021

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title = "Direct Synthesis of β-Amino Aldehydes from Linear Allylic Esters Using O2as the Sole Oxidant",

abstract = "A tandem isomerization-anti-Markovnikov oxidation of linear allylic imidic esters is developed using bis(benzonitrile)palladium chloride as the catalyst and O2 as the sole oxidant, regiospecifically giving β-amino aldehydes as the product. tert-Butyl nitrite works as a simple, and the only, redox cocatalyst. tBuOH proves to be a crucial solvent for achieving excellent yield and specificity toward anti-Markovnikov aldehyde products.",

author = "Lei, {Shu Hui} and Ya Zhong and Cai, {Xian Peng} and Qing Huang and Qu, {Jian Ping} and Kang, {Yan Biao}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c03619",

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T1 - Direct Synthesis of β-Amino Aldehydes from Linear Allylic Esters Using O2as the Sole Oxidant

AU - Lei, Shu Hui

AU - Zhong, Ya

AU - Cai, Xian Peng

AU - Huang, Qing

AU - Qu, Jian Ping

AU - Kang, Yan Biao

PY - 2021/12/3

Y1 - 2021/12/3

N2 - A tandem isomerization-anti-Markovnikov oxidation of linear allylic imidic esters is developed using bis(benzonitrile)palladium chloride as the catalyst and O2 as the sole oxidant, regiospecifically giving β-amino aldehydes as the product. tert-Butyl nitrite works as a simple, and the only, redox cocatalyst. tBuOH proves to be a crucial solvent for achieving excellent yield and specificity toward anti-Markovnikov aldehyde products.

AB - A tandem isomerization-anti-Markovnikov oxidation of linear allylic imidic esters is developed using bis(benzonitrile)palladium chloride as the catalyst and O2 as the sole oxidant, regiospecifically giving β-amino aldehydes as the product. tert-Butyl nitrite works as a simple, and the only, redox cocatalyst. tBuOH proves to be a crucial solvent for achieving excellent yield and specificity toward anti-Markovnikov aldehyde products.

UR - http://www.scopus.com/inward/record.url?scp=85120384354&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c03619

DO - 10.1021/acs.orglett.1c03619

M3 - 文章

C2 - 34797081

AN - SCOPUS:85120384354

SN - 1523-7060

VL - 23

SP - 9273

EP - 9276

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Direct Synthesis of β-Amino Aldehydes from Linear Allylic Esters Using O₂as the Sole Oxidant

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