Efficient Synthesis of Helical Tetrasubstituted Alkenes as Potential Molecular Switches: A Two‐Component Palladium‐Catalyzed Triple Domino Process

A nickel-or palladium-catalyzed cascade approach to afford indolines-fused triazoles with tetrasubstituted olefins in good yields with excellent control of regio-and stereoselectivity is described. We have also discussed the synthesis of unsaturated carbonyl species when the alkyne was appended to an alkyl chain. The synthetic methodology has been extended to construct the biologically active spiroindoline core via a vinylcylopropane (VCP) intermedi-ate. The synthesized tetrasubstituted scaffolds were investigated for their photophysical properties and all of the them exhibited good absorption and fluorescence emission in the UV-visible region.Scheme 1. Scope of the reaction of aryl-substituted alkynyltriazoles with aryl halides.

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Nickel‐ or Palladium‐Catalyzed Stereoselective Synthesis of Tetrasubstituted Olefinic Indolines‐Fused Triazoles: Extension to the Spiroindoline Core

Senadi

Boominathan

et al. 2013

Adv Synth Catal

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Advances in Palladium‐Catalyzed Cascade Cyclizations

Biemolt

Ruijter

2018

Adv Synth Catal

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Thep ast decades in organic chemistry have witnessed significant improvements in synthetic efficiency as ar esult of considerable progress in cascade reactions,t andem reactions,a nd related onepot processes. These methods are less time-consuming andp roduce less waste comparedt ot he classical stepwise approach. However, cascade chemistry requires am ore careful design and compatible reaction types for success.P alladium-catalyzed cross-coupling reactions,w ith their well understoodm ultistep catalytic cycles,f orm ap romising basis for the design of cascade reactions.F urthermore,t hey are compatible with ar ange of functional groups and can be combined with ar ange of secondary transformations. Ther esulting palladium-catalyzed cascade reactions have provided access to ap lethorao fc omplex small molecules of high medicinal relevance.T his review providesa no verview of the developments in palladium-catalyzed cascade reactions since 2011, classified according to the initiation, propagation, andtermination steps comprising the palladium cascade reactions.T hisc lassification should assist the reader and may provide inspiration for the design of newc ascade reactions.

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Ein Dominoprozess zu Dibenzopentafulvalenen mittels vierfacher Carbopalladierung

et al. 2013

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Efficient Synthesis of Helical Tetrasubstituted Alkenes as Potential Molecular Switches: A Two‐Component Palladium‐Catalyzed Triple Domino Process

Cited by 22 publications

References 73 publications

Nickel‐ or Palladium‐Catalyzed Stereoselective Synthesis of Tetrasubstituted Olefinic Indolines‐Fused Triazoles: Extension to the Spiroindoline Core

Nickel‐ or Palladium‐Catalyzed Stereoselective Synthesis of Tetrasubstituted Olefinic Indolines‐Fused Triazoles: Extension to the Spiroindoline Core

Advances in Palladium‐Catalyzed Cascade Cyclizations

Ein Dominoprozess zu Dibenzopentafulvalenen mittels vierfacher Carbopalladierung

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