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Literature DB >> 34245074

C-Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes.

Ziyong Wang¹, Jason Wu¹, Walid Lamine², Bo Li¹, Jean-Marc Sotiropoulos², Anna Chrostowska², Karinne Miqueu², Shih-Yuan Liu^1,2.

Abstract

A new family of carbon-bound boron enolates, generated by a kinetically controlled halogen exchange between chlorocatecholborane and silylketene acetals, is described. These C-boron enolates are demonstrated to activate 1,3-enyne substrates in the presence of a Pd0 /Senphos ligand complex, resulting in the first examples of a carboboration reaction of an alkyne with enolate-equivalent nucleophiles. Highly substituted dienyl boron building blocks are produced in excellent site-, regio-, and diastereoselectivity by the described catalytic cis-carboboration reaction.

Entities: Chemical

Keywords: C−boron enolates; azaborine; carboboration; enyne; palladium

Year: 2021 PMID： 34245074 PMCID： PMC8440383 DOI： 10.1002/anie.202108534

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 16.823

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C-Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3-Enynes.

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