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- Title
Chemoselective Borane‐Catalyzed Hydroarylation of 1,3‐Dienes with Phenols.
- Authors
Wang, Guoqiang; Gao, Liuzhou; Chen, Hui; Liu, Xueting; Cao, Jia; Chen, Shengda; Cheng, Xu; Li, Shuhua
- Abstract
A B(C6F5)3‐catalyzed hydroarylation of a series of 1,3‐dienes with various phenols has been established through a combination of theoretical and experimental investigations, affording structurally diverse ortho‐allyl phenols. DFT calculations show that the reaction proceeds through a borane‐promoted protonation/Friedel–Crafts pathway involving a π‐complex of a carbocation–anion contact ion pair. This protocol features simple and mild reaction conditions, broad functional‐group tolerance, and low catalyst loading. The obtained ortho‐allyl phenols could be further converted into flavan derivatives using B(C6F5)3 with good cis diastereoselectivity. Furthermore, this transformation was applied in the late‐stage modification of pharmaceutical compounds.
- Subjects
CHEMOSELECTIVITY; BORANES; DIOLEFINS; PHENOLS; CARBOCATIONS
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 6, p1708
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201811729