Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 7, Pages 1493-1497Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob02557g
Keywords
-
Categories
Funding
- National Natural Science Foundation of China [21871045, 21703195]
- Natural Science Foundation of the Jilin Province [20190201070JC]
- Changchun University of Technology
Ask authors/readers for more resources
The Cu(i)-catalyzed ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent leads to the formation of cis-2-aryl-1,2-dihydronaphthalen-1-ol derivatives, differing from the trans-selectivity observed in similar Cu-catalyzed reactions with Grignard reagents. DFT calculations indicate a possible alternative pathway involving boronic ester by-product assisted ring-opening, instead of the canonical beta-oxygen elimination, as the rate-determining step.
The Cu(i)-catalyzed ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent provides access to cis-2-aryl-1,2-dihydronaphthalen-1-ol derivatives, in contrast to the exclusive trans-selectivity in related Cu-catalyzed reactions with Grignard reagents. DFT calculations suggest that the reaction possibly proceeds via boronic ester by-product assisted ring-opening as an alternative pathway to the canonical beta-oxygen elimination as the rate-determining step.
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