Cu-Catalyzedcis-selective ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent
- 26 January 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 19 (7), 1493-1497
- https://doi.org/10.1039/d0ob02557g
Abstract
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 β-oxygen elimination as the rate-determining step.Funding Information
- National Natural Science Foundation of China (21871045, 21703195)
- Department of Science and Technology of Jilin Province (20190201070JC)
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