One-Pot and Unsymmetrical Bis-Allylation of Malononitrile with Conjugated Dienes and Allylic Alcohols

Wenxiu Gao; Dong Zhang; Xiaoyu Zhang; Xinying Cai; Peizhong Xie; Teck Peng Loh

doi:10.1021/acs.orglett.2c03405

One-Pot and Unsymmetrical Bis-Allylation of Malononitrile with Conjugated Dienes and Allylic Alcohols

Wenxiu Gao, Dong Zhang, Xiaoyu Zhang, Xinying Cai, Peizhong Xie^*, Teck Peng Loh^*

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

A Pd/Ca catalytic system to promote the unsymmetrical bis-allylation of malononitrile was developed by selecting conjugated dienes and allylic alcohols as allylic reagents. This catalytic system suppressed the competitive symmetrical bis-allylation process and guaranteed the desired unsymmetrical bis-allylation with high chemoselectivity. A wide range of conjugated dienes and allylic alcohols were tolerated well in this transformation, and diverse 1,6-dienes were obtained with high efficiency.

Original language	English
Pages (from-to)	9355-9360
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	51
DOIs	https://doi.org/10.1021/acs.orglett.2c03405
Publication status	Published - Dec 30 2022
Externally published	Yes

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© 2022 American Chemical Society. All rights reserved.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A Pd/Ca catalytic system to promote the unsymmetrical bis-allylation of malononitrile was developed by selecting conjugated dienes and allylic alcohols as allylic reagents. This catalytic system suppressed the competitive symmetrical bis-allylation process and guaranteed the desired unsymmetrical bis-allylation with high chemoselectivity. A wide range of conjugated dienes and allylic alcohols were tolerated well in this transformation, and diverse 1,6-dienes were obtained with high efficiency.",

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T1 - One-Pot and Unsymmetrical Bis-Allylation of Malononitrile with Conjugated Dienes and Allylic Alcohols

AU - Gao, Wenxiu

AU - Zhang, Dong

AU - Zhang, Xiaoyu

AU - Cai, Xinying

AU - Xie, Peizhong

AU - Loh, Teck Peng

PY - 2022/12/30

Y1 - 2022/12/30

N2 - A Pd/Ca catalytic system to promote the unsymmetrical bis-allylation of malononitrile was developed by selecting conjugated dienes and allylic alcohols as allylic reagents. This catalytic system suppressed the competitive symmetrical bis-allylation process and guaranteed the desired unsymmetrical bis-allylation with high chemoselectivity. A wide range of conjugated dienes and allylic alcohols were tolerated well in this transformation, and diverse 1,6-dienes were obtained with high efficiency.

AB - A Pd/Ca catalytic system to promote the unsymmetrical bis-allylation of malononitrile was developed by selecting conjugated dienes and allylic alcohols as allylic reagents. This catalytic system suppressed the competitive symmetrical bis-allylation process and guaranteed the desired unsymmetrical bis-allylation with high chemoselectivity. A wide range of conjugated dienes and allylic alcohols were tolerated well in this transformation, and diverse 1,6-dienes were obtained with high efficiency.

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JO - Organic Letters

JF - Organic Letters

IS - 51

ER -

One-Pot and Unsymmetrical Bis-Allylation of Malononitrile with Conjugated Dienes and Allylic Alcohols

Abstract

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ASJC Scopus Subject Areas

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