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Stereodivergent Alkyne Reduction by using Water as the Hydrogen Source

Rao, Santhosh and Prabhu, Kandikere Ramaiah (2018) Stereodivergent Alkyne Reduction by using Water as the Hydrogen Source. In: CHEMISTRY-A EUROPEAN JOURNAL, 24 (52). pp. 13954-13962.

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Official URL: http://dx.doi.org/10.1002/chem.201803147

Abstract

A homogeneous Pd-catalyzed stereodivergent reduction of alkynes to Z and E alkenes by using H2O as the H-2 source is presented. Mediated by a diboron reagent, the transfer hydrogenation has been accomplished to yield the desired geometrical isomer by rational ligand selection. The switchable stereoselectivity achieved using simple phosphine ligands is generally excellent. D2O has also been used as a D-2 source for synthesizing the corresponding deuterated olefins. Supported by a gram-scale synthesis, the reaction can easily be scaled up making it an efficient way to prepare alkenes commercially as well. Mechanistic studies suggest formation of H-PdL2-OAc as the crucial step leading to the presence of two pathways involving H-Pd-B(OR)(2) and molecular H-2 as active intermediates.

Item Type: Journal Article
Additional Information: Copy right for this article belong to WILEY-V C H VERLAG GMBH
Keywords: diboron; palladium; reduction; stereodivergence; water
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 10 Oct 2018 15:15
Last Modified: 10 Oct 2018 15:15
URI: http://eprints.iisc.ac.in/id/eprint/60851

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