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

Citation

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, Different selectivities in the insertions into C(sp2)-H bonds: Benzofulvenes by Dual Gold catalysis competition experiment, Chemistry A European Journal, 24, (42) pp. 10766-10772. ISSN 1521-3765 (2018) [Refereed Article]

Copyright Statement

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

DOI: doi:10.1002/chem.201801031

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 Details

Item Type:Refereed Article
Keywords:dual gold catalysis, density functional theory, mechanistic elucidation
Research Division:Chemical Sciences
Research Group:Other Chemical Sciences
Research Field:Organometallic Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Babaahmadi, R (Mr Rasool Babaahmadi)
Author:Yates, B (Professor Brian Yates)
Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:128286
Year Published:2018
Funding Support:Australian Research Council (DP180100904)
Web of Science® Times Cited:1
Deposited By:Chemistry
Deposited On:2018-09-12
Last Modified:2018-10-01
Downloads:0

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