Imines in Stille-Type Cross-Coupling Reactions: A Multicomponent Synthesis of α-Substituted Amides

Jason L. Davis; Rajiv Dhawan; Bruce A. Arndtsen

doi:10.1002/anie.200352123

Imines in Stille-Type Cross-Coupling Reactions: A Multicomponent Synthesis of α-Substituted Amides

Jason L. Davis, Rajiv Dhawan, Bruce A. Arndtsen

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

48 Scopus citations

Abstract

An alternative to nucleophilic chemistry for the construction of α-substituted amides and amine derivatives from imines is provided by the Stille-type coupling of imines with organotin reagents and acid chlorides (see scheme). This Pd-catalyzed reaction is suitable for components with a range of functional groups and has been extended into a four-component-coupling reaction with carbon monoxide. dba = dibenzylideneacetone, RT = room temperature.

Original language	English (US)
Pages (from-to)	590-594
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	5
DOIs	https://doi.org/10.1002/anie.200352123
State	Published - Jan 23 2004
Externally published	Yes

Keywords

Amides
Imines
Multicomponent reactions
Palladium
Stille reaction

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200352123

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abstract = "An alternative to nucleophilic chemistry for the construction of α-substituted amides and amine derivatives from imines is provided by the Stille-type coupling of imines with organotin reagents and acid chlorides (see scheme). This Pd-catalyzed reaction is suitable for components with a range of functional groups and has been extended into a four-component-coupling reaction with carbon monoxide. dba = dibenzylideneacetone, RT = room temperature.",

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AU - Arndtsen, Bruce A.

PY - 2004/1/23

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AB - An alternative to nucleophilic chemistry for the construction of α-substituted amides and amine derivatives from imines is provided by the Stille-type coupling of imines with organotin reagents and acid chlorides (see scheme). This Pd-catalyzed reaction is suitable for components with a range of functional groups and has been extended into a four-component-coupling reaction with carbon monoxide. dba = dibenzylideneacetone, RT = room temperature.

KW - Amides

KW - Imines

KW - Multicomponent reactions

KW - Palladium

KW - Stille reaction

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Imines in Stille-Type Cross-Coupling Reactions: A Multicomponent Synthesis of α-Substituted Amides

Abstract

Keywords

ASJC Scopus subject areas

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