Microwave‐Accelerated Coupling‐Isomerization Reaction (MACIR) – A General Coupling‐Isomerization Synthesis of 1,3‐Diarylprop‐2‐en‐1‐ones

Schramm, Oana G.; Müller, Thomas J. J.

doi:10.1002/adsc.200600280

Cited by 45 publications

(2 citation statements)

References 34 publications

(9 reference statements)

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“…The reaction was carried out in tetrahydrofuran at 120 °C (dielectric heating) for 30 minutes with triethylamine as the base of choice (Scheme 3). These conditions were selected further to previous studies on the synthesis of chalcones.15, 16 The desired product 3a was obtained in 40% yield. From this encouraging result, we then optimized the reaction conditions.…”

Section: Scheme 2 Synthesis Of Chalcones Via a Microwave-assisted Cou...mentioning

confidence: 99%

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling-Isomerization Reaction

Müller¹,

Gendron²,

Davioud‐Charvet³

2013

Synthesis

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As a twofold Michael system, the diarylideneacetone core is of particular interest in organic synthesis and for therapeutic applications. To overcome the drawbacks of the classical Claisen-Schmidt protocol, a new methodology for the synthesis of dissymmetric (hetero)diarylideneacetones has been developed. Conditions were optimized with a Box-Behnken design of experiment. The milder reaction conditions allow the efficient preparation of fluorinated, or heteroaromatic, dissymmetric diarylideneacetones which cannot be obtained through the classical Claisen-Schmidt protocol.

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Section: Scheme 2 Synthesis Of Chalcones Via a Microwave-assisted Cou...mentioning

confidence: 99%

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling-Isomerization Reaction

Müller¹,

Gendron²,

Davioud‐Charvet³

2013

Synthesis

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“…Indeed, the practical solution for a general CIR turned out to be the microwave-assisted version of the CIR (MACIR) (Scheme 8). 23 Scheme 8 Microwave-assisted CIR (MACIR) of (hetero)aryl halides 1 and propargyl alcohols 2 to give (hetero)aryl enones 3…”

Section: General Microwave-assisted Coupling-isomerization Reaction (mentioning

confidence: 99%

Synthesis of Carbo- and Heterocycles via Coupling-Isomerization Reactions

Müller¹

2011

Synthesis

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The coupling-isomerization reaction is an unusual outcome of the Sonogashira coupling of propargyl alcohols, N-tosylamines, or ethers with preferentially electron-deficient (hetero)aryl halides. As a result, chalcones, enimines and allenyl ethers are generated in situ. The former two are readily transformed into heterocycles in consecutive cyclization and cyclocondensations in a onepot fashion, whereas the latter are excellent entries into pericyclic domino processes for the rapid construction of complex polycyclic scaffolds.

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Formation of Aldehydes and Ketones by Rearrangements

Larock

Dubrovskiy

Markina

2018

Comprehensive Organic Transformations

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Isomerization Epoxides Vinylic Ethers Pinacol and Related Rearrangements Ring Rearrangement Ring Opening Ring Contraction Ring Expansion Electrocyclic Rearrangements Miscellaneous Rearrangements

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Microwave‐Accelerated Coupling‐Isomerization Reaction (MACIR) – A General Coupling‐Isomerization Synthesis of 1,3‐Diarylprop‐2‐en‐1‐ones

Abstract: Abstract:The microwave-accelerated coupling-isomerization reaction (MACIR) of (hetero)aryl halides and propargyl alcohols represents a general Pd/Cu and base-catalyzed process for the synthesis of 3-arylprop-2-en-1-ones in good yields.

Cited by 45 publications

References 34 publications

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling-Isomerization Reaction

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling-Isomerization Reaction

Synthesis of Carbo- and Heterocycles via Coupling-Isomerization Reactions

Formation of Aldehydes and Ketones by Rearrangements

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Microwave‐Accelerated Coupling‐Isomerization Reaction (MACIR) – A General Coupling‐Isomerization Synthesis of 1,3‐Diarylprop‐2‐en‐1‐ones

Abstract: Abstract:The microwave-accelerated coupling-isomerization reaction (MACIR) of (hetero)aryl halides and propargyl alcohols represents a general Pd/Cu and base-catalyzed process for the synthesis of 3-arylprop-2-en-1-ones in good yields.

Cited by 45 publications

References 34 publications

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling-Isomerization Reaction

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed­ Coupling-Isomerization Reaction

Synthesis of Carbo- and Heterocycles via Coupling-Isomerization Reactions

Formation of Aldehydes and Ketones by Rearrangements

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Product

Resources

About

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling-Isomerization Reaction

Versatile Synthesis of Dissymmetric Diarylideneacetones via a Palladium-Catalyzed Coupling-Isomerization Reaction