Litcius/Paper detail

Stereoselective Unsymmetrical 1,1‐Diborylation of Alkynes with a Neutral sp<sup>2</sup>−sp<sup>3</sup> Diboron Reagent

Xiangyu Lou, Jiaxin Lin, Chun Yin Kwok, Hairong Lyu

2023Angewandte Chemie International Edition28 citationsDOIOpen Access PDF

Abstract

Abstract The incorporation of two distinct boryl groups at the same carbon center in organic molecules has attracted growing research interest due to its potential for facilitating controlled, precise synthesis through stepwise dual carbon‐boron bond transformations. Here we report a method to access u nsymmetrical 1,1‐ d i b oryl a lkene (UDBA) stereoselectively via the reaction of readily available alkynes with a neutral sp 2 −sp 3 diboron reagent (NHC) B H 2 ‐ B pin (NHC= N ‐heterocyclic carbene). Attributing to the chemically easily distinguishable nature of the sp 2 and sp 3 boryl moieties, controllable stepwise derivatization of the resultant UDBAs is realized. This process leads to various multifunctionalized olefins and organoborons, such as acylboranes, which are difficult to prepare by other methods.

Topics & Concepts

ReagentCarbeneChemistryBoronStereoselectivityDerivatizationMoleculeMedicinal chemistryCarbon fibersCombinatorial chemistryOrganic chemistryMaterials scienceCatalysisComposite numberComposite materialHigh-performance liquid chromatographyOrganoboron and organosilicon chemistryBoron Compounds in ChemistryCatalytic Cross-Coupling Reactions