Abstract
A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes-Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.
| Original language | English |
|---|---|
| Pages (from-to) | 4753-4758 |
| Number of pages | 6 |
| Journal | Synthesis (Germany) |
| Volume | 49 |
| Issue number | 21 |
| DOIs | |
| State | Published - 2 Nov 2017 |
Bibliographical note
Funding Information:National Research Foundation of Korea grant (NRF-2016R1A2B4011719) funded by the Korean government (MEST).
Publisher Copyright:
© Georg Thieme Verlag Stuttgart New York.
Keywords
- allylic substitution
- copper
- homoallylic boronates
- hydrocupration
- N-heterocyclic carbenes
- tandem reaction
Fingerprint
Dive into the research topics of 'NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates'. Together they form a unique fingerprint.Cite this
- APA
- Author
- BIBTEX
- Harvard
- Standard
- RIS
- Vancouver