Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates

Yanli Yin; Fang Chen; Dong Chen; Peizhong Xie; Dongping Wang; Teck Peng Loh

doi:10.1021/acs.orglett.4c04267

Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates

Yanli Yin, Fang Chen, Dong Chen, Peizhong Xie, Dongping Wang, Teck Peng Loh

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

1 Scopus citations

Abstract

We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita-Baylis-Hillman (MBH) acetates to synthesize E-type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity (E/Z ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.

Original language	English
Pages (from-to)	269-274
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.4c04267
State	Published - 10 Jan 2025
Externally published	Yes

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title = "Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates",

abstract = "We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita-Baylis-Hillman (MBH) acetates to synthesize E-type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity (E/Z ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.",

author = "Yanli Yin and Fang Chen and Dong Chen and Peizhong Xie and Dongping Wang and Loh, {Teck Peng}",

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doi = "10.1021/acs.orglett.4c04267",

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T1 - Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates

AU - Yin, Yanli

AU - Chen, Fang

AU - Chen, Dong

AU - Xie, Peizhong

AU - Wang, Dongping

AU - Loh, Teck Peng

PY - 2025/1/10

Y1 - 2025/1/10

N2 - We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita-Baylis-Hillman (MBH) acetates to synthesize E-type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity (E/Z ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.

AB - We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita-Baylis-Hillman (MBH) acetates to synthesize E-type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity (E/Z ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.

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DO - 10.1021/acs.orglett.4c04267

M3 - 文章

AN - SCOPUS:85213257776

SN - 1523-7060

VL - 27

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JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates

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