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- Title
Pd‐Catalyzed Tandem Pathway for Stereoselective Synthesis of (E)‐1,3‐Enyne from β‐Nitroalkenes by Using a Sacrificial Directing Group.
- Authors
Mondal, Subal; Midya, Siba P.; Das, Suman; Mondal, Soumya; Islam, Abu S. M.; Ghosh, Pradyut
- Abstract
The involvement of nitroalkenes instead of minimal one alkyne motif for (E)‐1,3‐enynes synthesis through a palladium catalyzed stereoselective bond forming pathway at room temperature is presented. Implication of nitro group as a sacrificial directing group, formation of magical alkyne on a newly developed Csp3‐Csp3 bond with initial palladium‐MBH adduct make this methodology distinctive. This protocol features an unprecedented sequential acetate addition, carbon‐carbon bond formation, isomerization of double bond and nitromethane degradation in a tandem catalytic walk via dancing hybridization. Mechanistic understanding through identification of intermediates and computational calculations furnishes complete insight into the tandem catalytic pathway. Broad substrates scope and functional groups tolerance make this synthetic methodology magnificent and dynamic. This represents the first example of stereoselective 1,3‐enyne synthesis exclusively from alkene substrates by introducing the concept of sacrificial directing group.
- Subjects
CARBON-carbon bonds; DOUBLE bonds; GROUP 15 elements; NITROALKENES; ALKENES
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 61, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202301637