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Different selectivities in the insertions into C(sp2)-H bonds: Benzofulvenes by Dual Gold catalysis competition experiment
journal contribution
posted on 2023-05-19, 21:12 authored by Plajer, AJ, Ahrens, L, Wieteck, M, Lustosa, DM, Rasool BabaahmadiRasool Babaahmadi, Brian YatesBrian Yates, Alireza AriafardAlireza Ariafard, Rudolph, M, Rominger, F, Hashmi, ASKAn unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)-H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C-H positions. A bidirectional synthesis with two competing ortho-aryl C-H bonds in the selectivity determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C-H bonds with a benzylic methyl group also showed perfect selectivity.
Funding
Australian Research Council
University of Wollongong
History
Publication title
ChemistryVolume
24Issue
42Pagination
10766-10772ISSN
1521-3765Department/School
School of Natural SciencesPublisher
WileyPlace of publication
GermanyRights statement
Copyright 2018 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimRepository Status
- Restricted