Journal
ACS CATALYSIS
Volume 11, Issue 12, Pages 6757-6762Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01500
Keywords
allylic alkylation; hydrogen atom transfer; C-H functionalization; palladium catalysis; combined catalysis
Categories
Funding
- University of Science and Technology of China
- Youth Innovation Promotion Association CAS
Ask authors/readers for more resources
A rapid synthetic method for a target compound has been developed by combining photocatalysis and palladium catalysis, demonstrating an atom-economic and environmentally friendly strategy. Experimental results suggest that this method has high synthetic utility.
The rapid assembly of an easily accessible terminal alkene, an aliphatic C(sp(3))-H coupling partner, and allyl carbonate has been established by merging hydrogen atom transfer photocatalyst-mediated nucleophile generation and palladium-catalyzed allylic alkylation. The synthetic utility of this strategy is embodied by a concise synthesis of (+/-)-mesembrine. Mechanistic studies suggest that this protocol proceeds via a radical/ionic relay process, and a carbanionic species serves as a key intermediate for nucleophile attack on pi-allylpalladium through a classic two-electron allylation pathway. This protocol showcases an atom-economic and environmentally friendly method to generate a nonstabilized nucleophile for transition-metal catalysis.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available