Integrated Approach\nfor Allyl Amine Synthesis Combining\nthe Decarboxylative Coupling of Arylacrylic Acids with the Petasis\nReaction

A metal-free multicomponent reaction\nstrategy for synthesizing\nallyl amines through decarboxylative coupling combined with the Petasis\nreaction is described. Utilizing (<i>E</i>)-3-(2,4,6-trimethoxyphenyl)acrylic\nacid, various boronic acids, a formaldehyde solution, and primary\namines, the method operates efficiently without metal catalysts. Investigations\nreveal that electron-donating substituents in cinnamic acid derivatives\nsignificantly enhance reactivity, which is crucial for effective transformations.\nUnder the optimized conditions, yields of ≤78% were obtained\nacross a diverse range of 30 allyl amines.

Publication Details

Journal
Figshare
Published
2024-09-15
DOI
https://doi.org/10.1021/acs.joc.4c01574.s001
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Integrated Approach\nfor Allyl Amine Synthesis Combining\nthe Decarboxylative Coupling of Arylacrylic Acids with the Petasis\nReaction

Figshare
Catalytic Cross-Coupling Reactions
article

Integrated Approach\nfor Allyl Amine Synthesis Combining\nthe Decarboxylative Coupling of Arylacrylic Acids with the Petasis\nReaction

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Abstract

A metal-free multicomponent reaction\nstrategy for synthesizing\nallyl amines through decarboxylative coupling combined with the Petasis\nreaction is described. Utilizing (<i>E</i>)-3-(2,4,6-trimethoxyphenyl)acrylic\nacid, various boronic acids, a formaldehyde solution, and primary\namines, the method operates efficiently without metal catalysts. Investigations\nreveal that electron-donating substituents in cinnamic acid derivatives\nsignificantly enhance reactivity, which is crucial for effective transformations.\nUnder the optimized conditions, yields of ≤78% were obtained\nacross a diverse range of 30 allyl amines.

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Openalex Percentile: Top 79%
Catalytic Cross-Coupling Reactions
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Integrated Approach\nfor Allyl Amine Synthesis Combining\nthe Decarboxylative Coupling of Arylacrylic Acids with the Petasis\nReaction · Figshare (2024) | TGRS Research Map | TGRS