142019 - Triarylborane-catalyzed alkenylation reactions of aryl esters with diazo compounds.pdf (2.21 MB)
Triarylborane-catalyzed alkenylation reactions of aryl esters with diazo compounds
journal contribution
posted on 2023-05-20, 19:44 authored by Dasgupta, A, Stefkova, K, Rasool BabaahmadiRasool Babaahmadi, Gierlichs, L, Alireza AriafardAlireza Ariafard, Melen, RLHerein we report a facile, mild reaction protocol to form carbon–carbon bonds in the absence of transition metal catalysts. We demonstrate the metal‐free alkenylation reactions of aryl esters with α‐diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.
Funding
Australian Research Council
University of Wollongong
History
Publication title
Angewandte ChemieVolume
59Issue
36Pagination
15492-15496ISSN
1433-7851Department/School
School of Natural SciencesPublisher
Wiley-V C H Verlag GmbhPlace of publication
Po Box 10 11 61, Weinheim, Germany, D-69451Rights statement
Copyright 2020 The Authors. Licensed under Creative Commons Attribution 4.0 International (CC BY 4.0) https://creativecommons.org/licenses/by/4.0/Repository Status
- Open