We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Palladium‐Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation.
- Authors
Liu, Chengwei; Ji, Chong‐Lei; Hong, Xin; Szostak, Michal
- Abstract
Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent‐enabled decarbonylation of the in situ accessible sterically‐hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late‐stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C−O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.
- Subjects
PALLADIUM; DECARBONYLATION; BORYLATION; CARBOXYLIC acids; AROMATIC compounds
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 51, p16963
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201810145