An in-mediated tandem reaction of aldehydes with 3-bromo-1-propyne to produce 1-substituted-3-methylene-5-yn-1-ol compounds

Jing Mei Huang; Hui Chao Luo; Zu Xing Chen; Gui Chun Yang; Teck Peng Loh

doi:10.1002/ejoc.200700758

An in-mediated tandem reaction of aldehydes with 3-bromo-1-propyne to produce 1-substituted-3-methylene-5-yn-1-ol compounds

Jing Mei Huang, Hui Chao Luo, Zu Xing Chen, Gui Chun Yang, Teck Peng Loh

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

7 Scopus citations

Abstract

A one-pot reaction for the synthesis of 1-substituted-3-methylene-5-yn-1-ol compounds from In-mediated propargylation of aldehydes with 3-bromo-1-propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively subjected to further propargylation of the triple bond to afford the Markovnikov addition products in a regiospecific fashion.

Original language	English
Pages (from-to)	295-298
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	2
DOIs	https://doi.org/10.1002/ejoc.200700758
State	Published - 2008
Externally published	Yes

Keywords

Alcohols
Aldehydes
Alkynes
Indium
Propargylation
Tandem

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10.1002/ejoc.200700758

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title = "An in-mediated tandem reaction of aldehydes with 3-bromo-1-propyne to produce 1-substituted-3-methylene-5-yn-1-ol compounds",

abstract = "A one-pot reaction for the synthesis of 1-substituted-3-methylene-5-yn-1-ol compounds from In-mediated propargylation of aldehydes with 3-bromo-1-propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively subjected to further propargylation of the triple bond to afford the Markovnikov addition products in a regiospecific fashion.",

keywords = "Alcohols, Aldehydes, Alkynes, Indium, Propargylation, Tandem",

author = "Huang, {Jing Mei} and Luo, {Hui Chao} and Chen, {Zu Xing} and Yang, {Gui Chun} and Loh, {Teck Peng}",

year = "2008",

doi = "10.1002/ejoc.200700758",

language = "英语",

pages = "295--298",

journal = "European Journal of Organic Chemistry",

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T1 - An in-mediated tandem reaction of aldehydes with 3-bromo-1-propyne to produce 1-substituted-3-methylene-5-yn-1-ol compounds

AU - Huang, Jing Mei

AU - Luo, Hui Chao

AU - Chen, Zu Xing

AU - Yang, Gui Chun

AU - Loh, Teck Peng

PY - 2008

Y1 - 2008

N2 - A one-pot reaction for the synthesis of 1-substituted-3-methylene-5-yn-1-ol compounds from In-mediated propargylation of aldehydes with 3-bromo-1-propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively subjected to further propargylation of the triple bond to afford the Markovnikov addition products in a regiospecific fashion.

AB - A one-pot reaction for the synthesis of 1-substituted-3-methylene-5-yn-1-ol compounds from In-mediated propargylation of aldehydes with 3-bromo-1-propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively subjected to further propargylation of the triple bond to afford the Markovnikov addition products in a regiospecific fashion.

KW - Alcohols

KW - Aldehydes

KW - Alkynes

KW - Indium

KW - Propargylation

KW - Tandem

UR - http://www.scopus.com/inward/record.url?scp=38349092997&partnerID=8YFLogxK

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DO - 10.1002/ejoc.200700758

M3 - 文章

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SN - 1434-193X

SP - 295

EP - 298

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 2

ER -

An in-mediated tandem reaction of aldehydes with 3-bromo-1-propyne to produce 1-substituted-3-methylene-5-yn-1-ol compounds

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Keywords

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