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- Title
Ni‐Catalyzed Linearizable Cyclization/Coupling with Detachable Silicon‐Oxygen Linker: Access to 1,2‐Oxasilolanes, 3‐Hydroxysilanes and 4‐Arylalkanols.
- Authors
Lakomy, Margaret G.; Shankar, Majji; Del Rio, Ava C.; Giri, Ramesh
- Abstract
We disclose a Ni‐catalyzed cyclization/alkylmetal interception reaction in which products are readily linearized to permit regiodefined alkene dicarbofunctionalization. This method offers a convenient route to access 1,2‐oxasilolane heterocycles, 3‐hydroxysilanes and 4‐arylalkanols with the formation of C(sp3)−C(sp3) bonds at primary and secondary alkyl carbon centers. In this reaction, a silicon‐oxygen (Si−O) bond functions as a detachable linker that can be delinked with several hydride, alkyl, aryl and vinyl nucleophiles to create profusely functionalized 3‐hydroxysilanes. A silicon motif in the cyclic C(sp3)−Si−O construct in 1,2‐oxasilolane heterocycles can also be selectively deleted by Pd‐catalyzed hydrodesilylation affording Si‐ablated linear alcohol products reminiscent of vicinal ethylene dicarbofunctionalization with C(sp3) and C(sp2) carbon sources.
- Subjects
RING formation (Chemistry); ALKENES; HETEROCYCLIC compounds; NUCLEOPHILES; HYDRIDES
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 24, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202404679