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- Title
Aluminium‐Catalyzed Selective Hydroboration of Esters and Epoxides to Alcohols: C−O Bond Activation.
- Authors
Sarkar, Nabin; Kumar Sahoo, Rajata; Nembenna, Sharanappa
- Abstract
In this work, the molecular aluminium dihydride complex bearing an N, N'‐chelated conjugated bis‐guanidinate (CBG) ligand is used as a catalyst for reducing a wide range of aryl and alkyl esters with good tolerance of alkene (C=C), alkyne (C≡C), halides (Cl, Br, I and F), nitrile (C≡N), and nitro (NO2) functionalities. Further, we investigated the catalytic application of aluminium dihydride in the C−O bond cleavage of alkyl and aryl epoxides into corresponding branched Markovnikov ring‐opening products. In addition, the chemoselective intermolecular reduction of esters over other reducible functional groups, such as amides and alkenes, has been established. Intermediates are isolated and characterized by NMR and HRMS studies, which confirm the probable catalytic cycles for the hydroboration of esters and epoxides.
- Subjects
EPOXY compounds; HYDROBORATION; ARYL esters; ESTERS; SCISSION (Chemistry); RING-opening reactions; HALIDES; MAGNESIUM hydride
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 4, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202203023