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[Pt(PPh<sub>3</sub>)<sub>4</sub>]-Catalyzed Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes

Jakub Szyling, Aleksandra Szymańska, Adrian Franczyk, Jędrzej Walkowiak

2022The Journal of Organic Chemistry16 citationsDOIOpen Access PDF

Abstract

P NMR studies. An alternative isolation method via product condensation on a cold finger was developed, which, in contrast to previous literature reports, eliminates the need for the additional transformation of rapidly decomposing enynyl pinacol boronates to more stable silica-based column chromatography derivatives during the separation step. To prove the efficiency of this simple catalytic protocol, bisboryl-functionalized enynes were synthesized in a gram scale and tested as useful building blocks in advanced organic transformations, such as hydrosilylation and Suzuki and sila-Sonogashira couplings. The presence of silyl, boryl, as well as other functions like halogen or alkoxy in their structures builds a new class of multifunctionalized enynes that might be modified in various chemical reactions.

Topics & Concepts

Sonogashira couplingPinacolCatalysisChemistryCombinatorial chemistryHalogenHydrosilylationCatalytic cycleBorylationAlkoxy groupOrganic chemistryPalladiumArylAlkylOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis
[Pt(PPh<sub>3</sub>)<sub>4</sub>]-Catalyzed Selective Diboration of Symmetrical and Unsymmetrical 1,3-Diynes | Litcius