Dehydrative Cross-Coupling of Allylic Alcohols with Alkynes

Peizhong Xie; Zuolian Sun; Shuangshuang Li; Lei Zhang; Xinying Cai; Weishan Fu; Xiaobo Yang; Yanan Liu; Xiangyang Wo; Teck Peng Loh

doi:10.1021/acs.orglett.0c00108

Dehydrative Cross-Coupling of Allylic Alcohols with Alkynes

Peizhong Xie^*, Zuolian Sun, Shuangshuang Li, Lei Zhang, Xinying Cai, Weishan Fu, Xiaobo Yang, Yanan Liu, Xiangyang Wo, Teck Peng Loh

^*Corresponding author for this work

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

26 Citations (Scopus)

Abstract

A highly efficient Pd/Ca catalytic system for the directly dehydrative cross-coupling of allylic alcohols with terminal alkynes was developed. This calcium salt cocatalyst facilitates the oxidative addition of the palladium catalyst (1 mol %) to the C-OH bond. Then, the in situ-generated hydroxide ion deprotonates the terminal alkynes to promote the formation of the allylalkynylpalladium intermediate, liberating water as the only byproduct. This proposed mechanism is also supported by density functional theory calculations. An anticancer agent was prepared from inexpensive starting materials on a 10 g scale.

Original language	English
Pages (from-to)	1599-1604
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.0c00108
Publication status	Published - Feb 21 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c00108

Cite this

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title = "Dehydrative Cross-Coupling of Allylic Alcohols with Alkynes",

abstract = "A highly efficient Pd/Ca catalytic system for the directly dehydrative cross-coupling of allylic alcohols with terminal alkynes was developed. This calcium salt cocatalyst facilitates the oxidative addition of the palladium catalyst (1 mol \%) to the C-OH bond. Then, the in situ-generated hydroxide ion deprotonates the terminal alkynes to promote the formation of the allylalkynylpalladium intermediate, liberating water as the only byproduct. This proposed mechanism is also supported by density functional theory calculations. An anticancer agent was prepared from inexpensive starting materials on a 10 g scale.",

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

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doi = "10.1021/acs.orglett.0c00108",

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T1 - Dehydrative Cross-Coupling of Allylic Alcohols with Alkynes

AU - Xie, Peizhong

AU - Sun, Zuolian

AU - Li, Shuangshuang

AU - Zhang, Lei

AU - Cai, Xinying

AU - Fu, Weishan

AU - Yang, Xiaobo

AU - Liu, Yanan

AU - Wo, Xiangyang

AU - Loh, Teck Peng

PY - 2020/2/21

Y1 - 2020/2/21

N2 - A highly efficient Pd/Ca catalytic system for the directly dehydrative cross-coupling of allylic alcohols with terminal alkynes was developed. This calcium salt cocatalyst facilitates the oxidative addition of the palladium catalyst (1 mol %) to the C-OH bond. Then, the in situ-generated hydroxide ion deprotonates the terminal alkynes to promote the formation of the allylalkynylpalladium intermediate, liberating water as the only byproduct. This proposed mechanism is also supported by density functional theory calculations. An anticancer agent was prepared from inexpensive starting materials on a 10 g scale.

AB - A highly efficient Pd/Ca catalytic system for the directly dehydrative cross-coupling of allylic alcohols with terminal alkynes was developed. This calcium salt cocatalyst facilitates the oxidative addition of the palladium catalyst (1 mol %) to the C-OH bond. Then, the in situ-generated hydroxide ion deprotonates the terminal alkynes to promote the formation of the allylalkynylpalladium intermediate, liberating water as the only byproduct. This proposed mechanism is also supported by density functional theory calculations. An anticancer agent was prepared from inexpensive starting materials on a 10 g scale.

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

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ER -

Dehydrative Cross-Coupling of Allylic Alcohols with Alkynes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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