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Different selectivities in the insertions into C(sp2)-H bonds: Benzofulvenes by Dual Gold catalysis competition experiment

Plajer, AJ, Ahrens, L, Wieteck, M, Lustosa, DM, Babaahmadi, R, Yates, B ORCID: 0000-0001-9663-3301, Ariafard, A ORCID: 0000-0003-2383-6380, Rudolph, M, Rominger, F and Hashmi, ASK 2018 , 'Different selectivities in the insertions into C(sp2)-H bonds: Benzofulvenes by Dual Gold catalysis competition experiment' , Chemistry A European Journal, vol. 24, no. 42 , pp. 10766-10772 , doi: 10.1002/chem.201801031.

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Abstract

An 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.

Item Type: Article
Authors/Creators:Plajer, AJ and Ahrens, L and Wieteck, M and Lustosa, DM and Babaahmadi, R and Yates, B and Ariafard, A and Rudolph, M and Rominger, F and Hashmi, ASK
Keywords: dual gold catalysis, density functional theory, mechanistic elucidation
Journal or Publication Title: Chemistry A European Journal
Publisher: Wiley
ISSN: 1521-3765
DOI / ID Number: 10.1002/chem.201801031
Copyright Information:

Copyright 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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