An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin

Shihui Liu; Xiaobei Chen; Yanwei Hu; Laiqi Yuan; Shaohua Chen; Ping Wu; Wei Wang; Shilei Zhang; Wei Zhang

doi:10.1002/adsc.201400782

An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin

Shihui Liu, Xiaobei Chen, Yanwei Hu, Laiqi Yuan, Shaohua Chen, Ping Wu, Wei Wang, Shilei Zhang, Wei Zhang

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

23 Scopus citations

Abstract

An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.

Original language	English (US)
Pages (from-to)	553-560
Number of pages	8
Journal	Advanced Synthesis and Catalysis
Volume	357
Issue number	2-3
DOIs	https://doi.org/10.1002/adsc.201400782
State	Published - Feb 9 2015
Externally published	Yes

Keywords

1,1-dibromo-1-alkenes
Dihydroxerulin
Terminal alkynes
Tetra-n-butylammonium fluoride
Triphenylphosphane

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201400782

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title = "An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin",

abstract = "An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.",

keywords = "1,1-dibromo-1-alkenes, Dihydroxerulin, Terminal alkynes, Tetra-n-butylammonium fluoride, Triphenylphosphane",

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doi = "10.1002/adsc.201400782",

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T1 - An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin

AU - Liu, Shihui

AU - Chen, Xiaobei

AU - Hu, Yanwei

AU - Yuan, Laiqi

AU - Chen, Shaohua

AU - Wu, Ping

AU - Wang, Wei

AU - Zhang, Shilei

AU - Zhang, Wei

PY - 2015/2/9

Y1 - 2015/2/9

N2 - An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.

AB - An efficient method of preparing various terminal alkynes from 1,1-dibromo-1-alkenes by using TBAF (tetra-n-butylammonium fluoride) as a base and triphenylphosphane as a reductant was developed. This method is strong base and low/high temperatures free, and can tolerate a broad range of substrates. These advantages were well demonstrated by the application of this method to the total synthesis of polyene natural product dihydroxerulin.

KW - 1,1-dibromo-1-alkenes

KW - Dihydroxerulin

KW - Terminal alkynes

KW - Tetra-n-butylammonium fluoride

KW - Triphenylphosphane

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An efficient method for the production of terminal alkynes from 1,1-dibromo-1-alkenes and its application in the total synthesis of natural product dihydroxerulin

Abstract

Keywords

ASJC Scopus subject areas

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