Regioselective synthesis of CF2Cl-substituted biaryls by [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4-aryl-1-chloro-1,1-difluoro-4-(trimethylsilyloxy)-3-en-2-ones

Specowius, Verena; Kelzhanova, Nazken K.; Abilov, Zharylkasyn A.; Langer, Peter

doi:10.1007/s00706-012-0795-4

Cited by 3 publications

References 18 publications

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Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

Rosenstein¹

2022

Organic Reactions

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This chapter describes the use of allyl‐ and vinylstannane reagents for a variety of radical‐based transformations. The processes discussed include direct addition of radicals to allyl‐ and vinylstannanes, multicomponent or multistep cascade reactions that terminate with an intermolecular allylation or vinylation, cyclizations onto allyl‐ or vinylstannane moieties, and allylstannylation reactions. Allylation reactions have provided a framework for the exploration of stereoselective radical reactions, and models for explaining the stereoselectivity obtained by a number of approaches are presented. Examples are provided to illustrate the scope of applications of allyl‐ and vinylstannane radical reactions in synthesis, as well as the ways that the newly introduced allyl and vinyl groups have been subsequently manipulated. A comparison is made to radical allylation and vinylation reactions that employ non‐tin‐based reagents.

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Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

Rosenstein¹

2022

Organic Reactions

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ChemInform Abstract: Regioselective Synthesis of CF₂Cl‐Substituted Biaryls by [3 + 3] Cyclocondensation of 1,3‐Bis(trimethylsilyloxy)‐1,3‐butadienes with 4‐Aryl‐1‐chloro‐1,1‐difluoro‐4‐(trimethylsilyloxy)‐3‐en‐2‐ones.

et al. 2012

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A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes

et al. 2014

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A metal-free one-pot cascade annulation of acyclic substrates dienaminodioate, cinnamaldehydes and allyl amine was achieved for the synthesis of polyfunctional biaryl-2-carbaldehydes. The reaction proceeds at room temperature by a trifluoroacetic acid mediated Diels-Alder pathway. Synthetic applications of the resulting biaryl-2-carbaldehyde have been demonstrated by conversion into an array of diverse molecules with biological and materials chemistry relevance. The present work offers a complementary route to the existing metal mediated cross-coupling methods for the preparation of biaryls.

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Regioselective synthesis of CF2Cl-substituted biaryls by [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4-aryl-1-chloro-1,1-difluoro-4-(trimethylsilyloxy)-3-en-2-ones

Cited by 3 publications

References 18 publications

Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

ChemInform Abstract: Regioselective Synthesis of CF₂Cl‐Substituted Biaryls by [3 + 3] Cyclocondensation of 1,3‐Bis(trimethylsilyloxy)‐1,3‐butadienes with 4‐Aryl‐1‐chloro‐1,1‐difluoro‐4‐(trimethylsilyloxy)‐3‐en‐2‐ones.

A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes

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Regioselective synthesis of CF2Cl-substituted biaryls by [3+3] cyclocondensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 4-aryl-1-chloro-1,1-difluoro-4-(trimethylsilyloxy)-3-en-2-ones

Cited by 3 publications

References 18 publications

Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

Radical Allylation, Vinylation, Allenylation, Alkynylation, and Propargylation Reactions Using Tin Reagents

ChemInform Abstract: Regioselective Synthesis of CF2Cl‐Substituted Biaryls by [3 + 3] Cyclocondensation of 1,3‐Bis(trimethylsilyloxy)‐1,3‐butadienes with 4‐Aryl‐1‐chloro‐1,1‐difluoro‐4‐(trimethylsilyloxy)‐3‐en‐2‐ones.

A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes

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ChemInform Abstract: Regioselective Synthesis of CF₂Cl‐Substituted Biaryls by [3 + 3] Cyclocondensation of 1,3‐Bis(trimethylsilyloxy)‐1,3‐butadienes with 4‐Aryl‐1‐chloro‐1,1‐difluoro‐4‐(trimethylsilyloxy)‐3‐en‐2‐ones.