Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds

Peizhong Xie; Xiangyang Wo; Xiaobo Yang; Xinying Cai; Shuangshuang Li; Cuiqing Gao; Weishan Fu; Zuolian Sun; Teck Peng Loh

doi:10.1039/c9gc02635e

Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds

Peizhong Xie^*, Xiangyang Wo, Xiaobo Yang, Xinying Cai, Shuangshuang Li, Cuiqing Gao, Weishan Fu, Zuolian Sun, Teck Peng Loh

^*Corresponding author for this work

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

15 Citations (Scopus)

Abstract

A novel calcium-catalyzed in situ dehydrative cross-coupling reaction of propargylic alcohols with 1,3-dicarbonyl compounds was developed. This catalytic system can suppress the competitive Meyer-Schuster rearrangement, control regioselectivity, and enable the desired process to occur under solvent-free conditions at room temperature with water as the only byproduct. A variety of vicinal tertiary and all-carbon quaternary centers can be obtained in high yields with broad functional group tolerance.

Original language	English
Pages (from-to)	5207-5211
Number of pages	5
Journal	Green Chemistry
Volume	21
Issue number	19
DOIs	https://doi.org/10.1039/c9gc02635e
Publication status	Published - 2019
Externally published	Yes

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Publisher Copyright:
© 2019 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Environmental Chemistry
Pollution

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title = "Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds",

abstract = "A novel calcium-catalyzed in situ dehydrative cross-coupling reaction of propargylic alcohols with 1,3-dicarbonyl compounds was developed. This catalytic system can suppress the competitive Meyer-Schuster rearrangement, control regioselectivity, and enable the desired process to occur under solvent-free conditions at room temperature with water as the only byproduct. A variety of vicinal tertiary and all-carbon quaternary centers can be obtained in high yields with broad functional group tolerance.",

author = "Peizhong Xie and Xiangyang Wo and Xiaobo Yang and Xinying Cai and Shuangshuang Li and Cuiqing Gao and Weishan Fu and Zuolian Sun and Loh, \{Teck Peng\}",

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year = "2019",

doi = "10.1039/c9gc02635e",

language = "English",

volume = "21",

pages = "5207--5211",

journal = "Green Chemistry",

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T1 - Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds

AU - Xie, Peizhong

AU - Wo, Xiangyang

AU - Yang, Xiaobo

AU - Cai, Xinying

AU - Li, Shuangshuang

AU - Gao, Cuiqing

AU - Fu, Weishan

AU - Sun, Zuolian

AU - Loh, Teck Peng

PY - 2019

Y1 - 2019

N2 - A novel calcium-catalyzed in situ dehydrative cross-coupling reaction of propargylic alcohols with 1,3-dicarbonyl compounds was developed. This catalytic system can suppress the competitive Meyer-Schuster rearrangement, control regioselectivity, and enable the desired process to occur under solvent-free conditions at room temperature with water as the only byproduct. A variety of vicinal tertiary and all-carbon quaternary centers can be obtained in high yields with broad functional group tolerance.

AB - A novel calcium-catalyzed in situ dehydrative cross-coupling reaction of propargylic alcohols with 1,3-dicarbonyl compounds was developed. This catalytic system can suppress the competitive Meyer-Schuster rearrangement, control regioselectivity, and enable the desired process to occur under solvent-free conditions at room temperature with water as the only byproduct. A variety of vicinal tertiary and all-carbon quaternary centers can be obtained in high yields with broad functional group tolerance.

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U2 - 10.1039/c9gc02635e

DO - 10.1039/c9gc02635e

M3 - Article

AN - SCOPUS:85072933359

SN - 1463-9262

VL - 21

SP - 5207

EP - 5211

JO - Green Chemistry

JF - Green Chemistry

IS - 19

ER -

Calcium-catalyzed regioselective dehydrative cross-coupling of propargylic alcohols with 1,3-dicarbonyl compounds

Abstract

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ASJC Scopus Subject Areas

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