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^*

^*Corresponding author for this work

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

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
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.4c04267
Publication status	Accepted/In press - 2024
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2024 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.4c04267

Cite this

@article{47ec74f4177e4571870c64de1ddca347,

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}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

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

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

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 - 2024

Y1 - 2024

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.

UR - http://www.scopus.com/inward/record.url?scp=85213257776&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85213257776&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.4c04267

DO - 10.1021/acs.orglett.4c04267

M3 - Article

AN - SCOPUS:85213257776

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this