Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 52, Pages 13954-13962Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803147
Keywords
diboron; palladium; reduction; stereodivergence; water
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Funding
- SERB, New Delhi [SB/S1/OC-56/2013]
- CSIR, New Delhi [02(0226)15/EMR-II]
- Indian Institute of Science
- RL Fine Chem
- UGC, New Delhi
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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.
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