叔膦介导的叠氮化合物与不饱和酮的连续Staudinger/Aza-Michael加成反应合成β-氨基取代酮类化合物

Tiantian Cong; Huamin Wang; Yuanyuan Liu; Haihong Wu; Junliang Zhang

doi:10.6023/cjoc201906005

叔膦介导的叠氮化合物与不饱和酮的连续Staudinger/Aza-Michael加成反应合成β-氨基取代酮类化合物

Translated title of the contribution: Phosphine-Mediated Sequential Staudinger/Aza-Michael Addition of Azides with Unsaturated Ketones to Synthesize β-Amino Substituted Ketones

Tiantian Cong
, Huamin Wang
, Yuanyuan Liu^*
, Haihong Wu
, Junliang Zhang

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

4 Scopus citations

Abstract

A phosphine-mediated Staudinger/Aza-Michael addition of azides with trifluoromethyl substituted α,β-unsaturated ketones was developed, giving hydroamination products in medium to good yields (up to 96%). The hydroamination products could be prepared on gram scale and a wide range of substrates are tolerated under the optimized reaction conditions (30 examples). ³¹P NMR experiments indicate that this reaction was initiated by Staudinger reaction of azide with phosphine.

Translated title of the contribution	Phosphine-Mediated Sequential Staudinger/Aza-Michael Addition of Azides with Unsaturated Ketones to Synthesize β-Amino Substituted Ketones
Original language	Chinese (Traditional)
Pages (from-to)	2157-2165
Number of pages	9
Journal	Chinese Journal of Organic Chemistry
Volume	39
Issue number	8
DOIs	https://doi.org/10.6023/cjoc201906005
State	Published - 1 Aug 2019

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title = "叔膦介导的叠氮化合物与不饱和酮的连续Staudinger/Aza-Michael加成反应合成β-氨基取代酮类化合物",

abstract = "A phosphine-mediated Staudinger/Aza-Michael addition of azides with trifluoromethyl substituted α,β-unsaturated ketones was developed, giving hydroamination products in medium to good yields (up to 96\%). The hydroamination products could be prepared on gram scale and a wide range of substrates are tolerated under the optimized reaction conditions (30 examples). 31P NMR experiments indicate that this reaction was initiated by Staudinger reaction of azide with phosphine.",

keywords = "Alkenes, Aza-Michael addition, Azides, Hydroamination, Phosphines, Staudinger reaction",

author = "Tiantian Cong and Huamin Wang and Yuanyuan Liu and Haihong Wu and Junliang Zhang",

note = "Publisher Copyright: {\textcopyright} 2019 Chinese Chemical Society \& SIOC, CAS.",

year = "2019",

month = aug,

day = "1",

doi = "10.6023/cjoc201906005",

language = "繁体中文",

volume = "39",

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journal = "Chinese Journal of Organic Chemistry",

issn = "0253-2786",

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T1 - 叔膦介导的叠氮化合物与不饱和酮的连续Staudinger/Aza-Michael加成反应合成β-氨基取代酮类化合物

AU - Cong, Tiantian

AU - Wang, Huamin

AU - Liu, Yuanyuan

AU - Wu, Haihong

AU - Zhang, Junliang

PY - 2019/8/1

Y1 - 2019/8/1

N2 - A phosphine-mediated Staudinger/Aza-Michael addition of azides with trifluoromethyl substituted α,β-unsaturated ketones was developed, giving hydroamination products in medium to good yields (up to 96%). The hydroamination products could be prepared on gram scale and a wide range of substrates are tolerated under the optimized reaction conditions (30 examples). 31P NMR experiments indicate that this reaction was initiated by Staudinger reaction of azide with phosphine.

AB - A phosphine-mediated Staudinger/Aza-Michael addition of azides with trifluoromethyl substituted α,β-unsaturated ketones was developed, giving hydroamination products in medium to good yields (up to 96%). The hydroamination products could be prepared on gram scale and a wide range of substrates are tolerated under the optimized reaction conditions (30 examples). 31P NMR experiments indicate that this reaction was initiated by Staudinger reaction of azide with phosphine.

KW - Alkenes

KW - Aza-Michael addition

KW - Azides

KW - Hydroamination

KW - Phosphines

KW - Staudinger reaction

UR - https://www.scopus.com/pages/publications/85072667906

U2 - 10.6023/cjoc201906005

DO - 10.6023/cjoc201906005

M3 - 文章

AN - SCOPUS:85072667906

SN - 0253-2786

VL - 39

SP - 2157

EP - 2165

JO - Chinese Journal of Organic Chemistry

JF - Chinese Journal of Organic Chemistry

IS - 8

ER -

叔膦介导的叠氮化合物与不饱和酮的连续Staudinger/Aza-Michael加成反应合成β-氨基取代酮类化合物

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