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- Title
Ligand‐Enabled β‐Methylene C(sp<sup>3</sup>)−H Arylation of Masked Aliphatic Alcohols.
- Authors
Xia, Guoqin; Zhuang, Zhe; Liu, Luo‐Yan; Schreiber, Stuart L.; Melillo, Bruno; Yu, Jin‐Quan
- Abstract
Despite recent advances, reactivity and site‐selectivity remain significant obstacles for the practical application of C(sp3)−H bond functionalization methods. Here, we describe a system that combines a salicylic‐aldehyde‐derived L,X‐type directing group with an electron‐deficient 2‐pyridone ligand to enable the β‐methylene C(sp3)−H arylation of aliphatic alcohols, which has not been possible previously. Notably, this protocol is compatible with heterocycles embedded in both alcohol substrates and aryl coupling partners. A site‐ and stereo‐specific annulation of dihydrocholesterol and the synthesis of a key intermediate of englitazone illustrate the practicality of this method.
- Subjects
ARYLATION; ALIPHATIC alcohols; METHYLENE group; ANNULATION; HETEROCYCLIC compounds
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 20, p7857
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202000632